TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE Chemical Properties

Boiling point:

374.2±42.0 °C(Predicted)

Density 

1.353±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

-1.55±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C14H18BrNO2/c1-14(2,3)18-13(17)16-7-6-10-4-5-12(15)8-11(10)9-16/h4-5,8H,6-7,9H2,1-3H3

InChIKey

PWPKRLMPHNRWHK-UHFFFAOYSA-N

SMILES

C1C2=C(C=CC(Br)=C2)CCN1C(OC(C)(C)C)=O

TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE Usage And Synthesis

Synthesis

To a mixed solution of 7-bromo-1,2,3,4-tetrahydroisoquinoline (1 g, 4.71 mmol) and sodium carbonate (1 g, 9.4 mmol) in tetrahydrofuran/water (16 mL/6 mL) was added di-tert-butyl dicarbonate (1.51 mL, 7.06 mmol). The reaction mixture was stirred at room temperature overnight. After the reaction was completed, the reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate as a colorless oil (1.46 g, 100% yield).

References

[1] Patent: WO2014/89324, 2014, A1. Location in patent: Paragraph 0240
[2] Patent: CN104016979, 2017, B. Location in patent: Paragraph 0620; 0621
[3] Patent: US2010/240671, 2010, A1. Location in patent: Page/Page column 58
[4] Patent: WO2017/1853, 2017, A1. Location in patent: Page/Page column 42-43
[5] Patent: CN105524045, 2016, A. Location in patent: Paragraph 0274; 0275; 0276

TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE(258515-65-0)Related Product Information

• 7-bromo-4H-chromen-4-one
• 7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine
• 7-BROMO-1H-INDOLE-3-CARBALDEHYDE
• 6-Tributylstannyl[1,2,4]triazolo[1,5-a]pyridine
• 7-BROMO-1,2,3,4-TETRAHYDRO-ISOQUINOLINE
• 7-BroMo-3-MethyliMidazo[1,5-a]pyridine
• 7-Bromo[1,2,4]triazolo[1,5-a]pyridine
• [[(6-BROMO)-2-PYRIDINYL]METHYL]-CARBAMIC ACID, 1,1-DIMETHYLETHYL ESTER
• TERT-BUTYL 8-HYDROXY-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE
• tert-butyl N-[(2-methylpyridin-3-yl)methyl]carbamate
• tert-butyl N-[(2-chloropyridin-4-yl)Methyl]carbaMate
• tert-Butyl 7-broMo-3,4-dihydroquinoline-1(2H)-carboxylate
• 2(1H)-Isoquinolinecarboxylic acid, 7-bromo-3,4-dihydro-6-methyl-, 1,1-dimethylethyl ester
• tert-butyl 6-hydroxy-5-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• tert-butyl 6-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate