3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE Chemical Properties

Melting point:

>143°C (dec.)

Boiling point:

620.5±55.0 °C(Predicted)

Density 

1.188±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Very Slightly, Heated)

pka

16.89±0.30(Predicted)

form 

Solid

color 

Light Beige

InChI

InChI=1S/C29H25NO2/c1-21-27-18-26(32-20-23-10-6-3-7-11-23)16-17-28(27)30-29(21)24-12-14-25(15-13-24)31-19-22-8-4-2-5-9-22/h2-18,30H,19-20H2,1H3

InChIKey

KRIJKJMYOVWRSJ-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(OCC3=CC=CC=C3)C=C2)C(C)=C1C1=CC=C(OCC2=CC=CC=C2)C=C1

Safety Information

HS Code 

29339900

3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE Usage And Synthesis

Uses

3-Methyl-5-(phenylmethoxy)-2-[4-(phenylmethoxy)phenyl]-1H-indole is an intermediate of Bazedoxifene acetate (B129250).

Synthesis

General procedure for the synthesis of 3-methyl-5-benzyloxy-2-(4-benzyloxyphenyl)-1H-indole from 4'-benzyloxy-2-bromophenyl acetone and 4-benzyloxyaniline hydrochloride: 10 g of 4'-benzyloxy-2-bromophenyl acetone (II-a), 15 g of p-benzyloxyaniline hydrochloride (II-b), 50 mL of N,N-dimethylformamide and 8 mL of triethylamine were mixed and reacted at 115 °C for 4 hours. Upon completion of the reaction, the progress of the reaction was monitored by thin layer chromatography (TLC). The reaction solution was slowly poured into 250 mL of ice water and a solid was precipitated. The crude product was collected, washed with 20 mL of methanol and dried under vacuum at 40 °C for 24 h. 12.5 g of yellow-brown solid product, 5-benzyloxy-2-[(4-benzyloxy)phenyl]-3-methyl-1H-indole (Intermediate II), was obtained in 94.6% yield.

References

[1] Patent: CN106810487, 2017, A. Location in patent: Paragraph 0078-0083; 0096; 0110; 0117
[2] Patent: CN104098499, 2016, B. Location in patent: Paragraph 0035-0037
[3] Chemico-Biological Interactions, 2012, vol. 197, # 1, p. 8 - 15
[4] Patent: WO2011/22596, 2011, A2. Location in patent: Page/Page column 4; 21; 22
[5] Journal of Medicinal Chemistry, 2001, vol. 44, # 11, p. 1654 - 1657

3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE(198479-63-9)Related Product Information

• Bazedoxifene Impurity 8
• Des(1-azepanyl)ethyl Bazedoxifene
• 1-[2-[4-(Chloromethyl)phenoxy]ethyl]hexahydro-1H-azepine
• 3-(4-METHYLBENZYLIDENE)CAMPHOR?
• Hydrogen
• BAZEDOXIFENE ACETATE
• BenzeneMethanol, 4-[2-(hexahydro-1H-azepin-1-yl)ethoxy]- (hydrochloride)
• 4-[2-(1-AZEPANYL)ETHOXY]BENZYL CHLORIDE HCL
• Bazedoxifene iMpurity 1
• Bazedoxifene-d4 Acetate
• 5-O-Benzylbazedoxifene
• 1-[[4-[2-(Hexahydro-1-oxido-1H-azepin-1-yl)ethoxy]phenyl]Methyl]-2-(4-hydroxyphenyl)-3-Methyl-1H-indol-5-ol
• Bazedoxifene impurity 6
• Bazedoxifene impurity 5
• 1-[4-(2-AZEPAN-1-YL-ETHOXY)-BENZYL]-5-BENZYLOXY-2-(4-BENZYLOXY-PHENYL)-3-METHYL-1H-INDOLE
• Bazedoxifene Impurity 10
• 3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE
• 2-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE