Ethyl Acetate → HCID 57992290, compound

HRID 1921241Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[Cl:30].[Cu](C#N)[C:32]#[N:33].C(OCC)(=O)C>CN(C)C=O>[Cl:30][C:3]1[CH:4]=[C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:17][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:32]#[N:33]

Participants

Conditions

Temperature: 200 °C

Procedure

2.48 g 1-(4-bromo-3-chloro-benzenesulfonyl)-5-(4-trifluoromethyl-phenyl)-2,3-dihydro-1H-indole were dissolved in 10 ml dimethylformamide. 2.15 g copper cyanide were added and the resulting mixture stirred under microwave irradiation at 200° C. for thirty minutes. The mixture was diluted by addition of 100 ml ethyl acetate and washed five times with portions of 50 ml saturated ammonium chloride solution. The organic layer was dried over MgSO4 then the solvent was removed in vacuo to obtain 935 mg crude 2-chloro-4-[5-(4-trifluoromethyl-phenyl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile. This material was used without further purification.

Workup

washwashed five times with portions of 50 ml saturated ammonium chloride solution
dry with materialThe organic layer was dried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-7a09f392915543e08d2e60cb535f5c49
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173674B2

Reaction notes

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