4-(2-Bromo-1,3-thiazol-5-yl)-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrile → 4-(4-Chlorophenyl)-3-methyl-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrile

HRID 561559Notes

Reaction equation

HRID 561559 reaction equation
CS(O[CH2:6][CH:7]([CH3:28])[CH:8]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)[C:9]1[C:17]2[C:12](=[C:13]([CH2:18][S:19][CH3:20])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=O)=O.Br[C:30]1SC(C(C2C3C(=C(CSC)C=CC=3)NC=2)CCC#N)=C[N:34]=1>CS(C)=O>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([CH:8]([C:9]2[C:17]3[C:12](=[C:13]([CH2:18][S:19][CH3:20])[CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)[CH:7]([CH3:28])[CH2:6][C:30]#[N:34])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 583921014-(2-Bromo-1,3-thiazol-5-yl)-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrileHCID 583924653-(4-Chlorophenyl)-2-methyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propyl methanesulfonate

Product 1

HCID 583921084-(4-Chlorophenyl)-3-methyl-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared starting from 215 mg (0.49 mmol) of the compound from Example 71A in analogy to the synthesis of the compound from Example 53, but with dimethyl sulfoxide as solvent. 177 mg (98% of theory) of the target compound were obtained as mixture of diastereomers.

Workup

  1. custom177 mg (98% of theory) of the target compound were obtained as mixture of diastereomers

Sources & evidence

ORD record
ord-a1a6824b6d814218a90641526cf03292
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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