3-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indole → 3-[(2-Chloro-4-fluorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfanyl) methyl]-1H-indole

HRID 561664Notes

Reaction equation

HRID 561664 reaction equation
[F:1]C1C=C2C(=C(CSC)C=1)NC=C2.[Cl:14][C:15]1[CH:20]=[C:19](F)[C:18](C(C2CC2)O)=[C:17]([F:27])[CH:16]=1.ClC1C=CC([CH:35]([CH:48]2[CH2:50][CH2:49]2)[C:36]2[C:44]3[C:39](=[C:40]([CH2:45][S:46][CH3:47])[CH:41]=[CH:42][CH:43]=3)[NH:38][CH:37]=2)=CC=1>>[Cl:14][C:15]1[CH:16]=[C:17]([F:27])[CH:18]=[CH:19][C:20]=1[CH:35]([CH:48]1[CH2:49][CH2:50]1)[C:36]1[C:44]2[C:39](=[C:40]([CH2:45][S:46][CH3:47])[CH:41]=[C:42]([F:1])[CH:43]=2)[NH:38][CH:37]=1

Participants

4

Reactant 3

HCID 583921383-[(4-Chlorophenyl)(cyclopropyl)methyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indoleHCID 58392245(4-Chloro-2,6-difluorophenyl)(cyclopropyl)methanol

Product 1

HCID 583924223-[(2-Chloro-4-fluorophenyl)(cyclopropyl)methyl]-5-fluoro-7-[(methylsulfanyl) methyl]-1H-indole

Procedure

The title compound was prepared starting from 200 mg (1.02 mmol) of the compound from Example 11A and 206 mg (1.02 mmol) of the compound from Example 156A in analogy to the synthesis of the compound from Example 227. 247 mg (64% of theory) of the target compound were obtained.

Workup

  1. custom247 mg (64% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-75be6ef4c98644fbb6c6807574c0d6b1
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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