| Identification | Back Directory | [Name]
3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE | [CAS]
198479-63-9 | [Synonyms]
5-(BenzyL
5-(Benzyloxy)
oxy)-2-(4-(benzyL
Bazedoxifene Impurity 11
Bazedoxifene intermediate I
3-METHYL-5-(PHENYLMETHOXY)-2-[4-(PHENYLMETHOXY)PHENYL]-1H-INDOLE
1H-Indole, 3-Methyl-5-(phenylMethoxy)-2-[4-(phenylMethoxy)phenyl]- | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C29H25NO2 | [MDL Number]
MFCD04004106 | [MOL File]
198479-63-9.mol | [Molecular Weight]
419.51 |
| Chemical Properties | Back Directory | [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) | [form ]
Solid | [pka]
16.89±0.30(Predicted) | [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 |
| Hazard Information | Back Directory | [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 |
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