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

HRID 561558Notes

Reaction equation

HRID 561558 reaction equation
CS(O[CH2:6][CH:7]([CH3:31])[CH:8]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(=O)=O.Br[C:33]1SC(C(C2C3C(=C(CSC)C=CC=3)NC=2)CCC#N)=C[N:37]=1>CS(C)=O>[CH3:31][CH:7]([CH:8]([C:19]1[C:27]2[C:22](=[C:23]([CH2:28][S:29][CH3:30])[CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:18])[F:17])=[CH:11][CH:10]=1)[CH2:6][C:33]#[N:37]

Participants

4

Reactant 2

HCID 583921014-(2-Bromo-1,3-thiazol-5-yl)-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}butanonitrileHCID 583921842-Methyl-3-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}-3-[4-(trifluoromethyl)phenyl]propyl methanesulfonate

Product 1

HCID 583924793-Methyl-4-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}-4-[4-(trifluoromethyl)phenyl]butanonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared starting from 620 mg (1.32 mmol) of the compound from Example 70A in analogy to the synthesis of the compound from Example 53 but with dimethyl sulfoxide as solvent. 492 mg (93% of theory) of the target compound were obtained as mixture of diastereomers.

Workup

  1. custom492 mg (93% of theory) of the target compound were obtained as mixture of diastereomers

Sources & evidence

ORD record
ord-e8b970b7f94b4093acfe2e3aad8f9279
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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