7-[(Methylsulfanyl)methyl]-1H-indole → 3-[1-(4-Chlorophenyl)-1-cyclopropylpropyl]-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561641Notes

Reaction equation

HRID 561641 reaction equation
[CH3:1][S:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.[CH:13]1([C:16]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)(O)[CH2:17][CH3:18])[CH2:15][CH2:14]1.C1(C(C2C3C(=C(CSC)C=CC=3)NC=2)(C2C=CC(OC)=C(F)C=2)C)CC1>>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:16]([C:9]2[C:8]3[C:12](=[C:4]([CH2:3][S:2][CH3:1])[CH:5]=[CH:6][CH:7]=3)[NH:11][CH:10]=2)([CH:13]2[CH2:15][CH2:14]2)[CH2:17][CH3:18])=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583923303-[1-Cyclopropyl-1-(3-fluoro-4-methoxyphenyl)ethyl]-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583925071-Cyclopropyl-1-(4-chlorophenyl)propanol

Product 1

HCID 583921183-[1-(4-Chlorophenyl)-1-cyclopropylpropyl]-7-[(methylsulfanyl)methyl]-1H-indole

Procedure

The title compound was prepared starting from 84 mg (0.48 mmol) of the compound from Example 8A and 100 mg (0.48 mmol) of the compound from Example 145A in analogy to the synthesis of the compound from Example 186. 38 mg (21% of theory) of the target compound were obtained.

Workup

  1. custom38 mg (21% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-6b98884d3c924f6f9e7ed9854d2eac07
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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