ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product Name: ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate
CAS No.: 1059630-08-8
Chemical Name: ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate
Synonyms: EOS-60905;Lumateperone Impurity 9;Lumateperone Impurity N10;3-(5-bromopyrimidin-2-yl)benzyl alcohol;ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3...;ethyl (4aS,9bR)-6-bromo-1H,2H,3H,4H,4aH,5H,9bH-pyrido[4,3-b]indole-2-carboxylate;ethyl (4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydropyrido[4,3-b]indole-2-carboxylate;ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate;Ethyl (4aS,9bR)-6-Bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate;(Sethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate
CBNumber: CB83142930
Molecular Formula: C14H17BrN2O2
Formula Weight: 325.2
MOL File: 1059630-08-8.mol

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ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate Property

Boiling point:: 406.8±45.0 °C(Predicted)
Density: 1.426±0.06 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
pka: 3.91±0.20(Predicted)
Appearance: White to off-white Solid
InChI: InChI=1S/C14H17BrN2O2/c1-2-19-14(18)17-7-6-12-10(8-17)9-4-3-5-11(15)13(9)16-12/h3-5,10,12,16H,2,6-8H2,1H3/t10-,12-/m0/s1
InChIKey: YKRFDXKYULKKPS-JQWIXIFHSA-N
SMILES: N1C2=C(C=CC=C2Br)[C@]2([H])CN(C(OCC)=O)CC[C@]12[H]

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

American Custom Chemicals Corporation

Product number: CCH0066019
Product name: ETHYL-(4AS,9BR)-6-BROMO-1H,2H,3H,4H,4AH,5H,9BH-PYRIDO[4,3-B]INDOLE-2-CARBOXYLATE
Purity: 95.00%
Packaging: 5MG
Price: $458.85
Updated: 2021/12/16

Crysdot

Product number: CD11358428
Product name: (4aS,9bR)-Ethyl6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate
Purity: 97%
Packaging: 5g
Price: $534
Updated: 2021/12/16

Alichem

Product number: 1059630088
Product name: (4aS,9bR)-Ethyl6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate
Packaging: 5g
Price: $708.24
Updated: 2021/12/16

Alichem

Product number: 1059630088
Product name: (4aS,9bR)-Ethyl6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate
Packaging: 10g
Price: $1345.76
Updated: 2021/12/16

Ambeed

Product number: A433454
Product name: (4aS,9bR)-Ethyl6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate
Purity: 97%
Packaging: 100mg
Price: $38
Updated: 2021/12/16

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ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate Chemical Properties,Usage,Production

Synthesis

1059630-13-5

541-41-3

1059630-08-8

Example 3: Preparation of ethyl (4aS,9bR)-6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate Step 1: (4aS,9bR)-6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole (36.0 g, 0.142 mol) was dissolved in 50% aqueous sodium hydroxide to free the base, followed by extraction of the product with methyl tert-butyl ether (MTBE). Step 2: The above free base (36.0g, 0.142mol) was dissolved in THF (300mL), triethylamine (24mL) was added and cooled in an ice water bath. Ethyl chloroformate (13.5mL, 0.142mol) was slowly added dropwise over 1 hour using a syringe pump. After removing the ice water bath, the reaction mixture was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, it was filtered through a diatomaceous earth pad and the solvent was evaporated to afford ethyl (4aS,9bR)-6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate. 1H NMR (CDCl3, 300MHz): δ 1.20-1.35 (m, 3H), 1.73-1.85 (m, 1H), 1.85-1.99 (m, 1H), 3.22-3.52 (m, 3H), 3.52-3.66 (m, 1H), 3.66-3.95 (br, 1H), 3.95-4.21 (m, 4H), 6.60 (m, 4H). 4H), 6.60 (t, J = 7.7 Hz, 1H), 7.04 (d, J = 7.2 Hz, 1H), 7.20 (d, J = 8.1 Hz, 1H). Alternative method: the (S)-mandelate of (4aS,9bR)-6-bromo-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole was used as starting material. To a 100 mL round bottom flask was added (S)-mandelate feedstock (5 g, 12.35 mmol), Na2CO3 (2.88 g, 27.17 mmol) and THF (25 mL). A solution of ethyl chloroformate (1.64 g, 15.11 mmol) in THF (5 mL) was added dropwise over 25 min at 25 °C. After the reaction mixture was stirred at 25 °C for 10 min, detection by HPLC showed less than 2% of starting material remaining and a product yield of about 98%. EtOH (12.5 mL) was added and about 30 mL of solvent (mostly THF) was removed by concentration under reduced pressure. H2O (37.5 mL) was added and the mixture was pH > 9. After stirring at room temperature for 1 hr, the product was filtered, the solid was washed with H2O (25 mL) and dried under vacuum at 58 °C for 16 hr to give a yellow solid of 3.9442 g (98% yield).1H NMR was consistent with the target product, and (S)-mandelic acid was not detected. hplc analysis showed a purity of the product of > 99%. lc-ms showed molecular ion peak M/e = 326 (M + 1).

References

[1] Patent: WO2008/112280, 2008, A1. Location in patent: Page/Page column 85-86

ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate Preparation Products And Raw materials

Raw materials

Preparation Products

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ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate Suppliers

China 59 India 1 United States 2 Global 62

Synthonix Inc

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Combi-Blocks Inc.

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View Lastest Price from ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Lumateperone Impurity 14 1059630-08-8
Price: US $0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 5g
Release date: 2025-03-25

1059630-08-8, ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylateRelated Search:

2H-Pyrido[4,3-b]indole-2-carboxylic acid, 6-bromo-1,3,4,4a,5,9b-hexahydro-, ethyl ester, (4aS,9bR)-

(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-Pyrido[4,3-b]indole-2-carboxylic acid ethyl ester

ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

(4aS,9bR)-Ethyl 6-bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate

ethyl (4aS,9bR)-6-bromo-1H,2H,3H,4H,4aH,5H,9bH-pyrido[4,3-b]indole-2-carboxylate

EOS-60905

(Sethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Lumateperone Impurity 9

ethyl(4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3...

Ethyl (4aS,9bR)-6-Bromo-3,4,4a,5-tetrahydro-1H-pyrido[4,3-b]indole-2(9bH)-carboxylate

Lumateperone Impurity N10

3-(5-bromopyrimidin-2-yl)benzyl alcohol

ethyl (4aS,9bR)-6-bromo-1,3,4,4a,5,9b-hexahydropyrido[4,3-b]indole-2-carboxylate

1059630-08-8