Pyridine → 2-Chloro-4-[5-(6-trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile

HRID 2192289Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[F:14][C:15]([F:32])([F:31])[C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH2:26][CH2:25]3)=[CH:18][CH:17]=1.N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:10]([N:27]2[C:28]3[C:24](=[CH:23][C:22]([C:19]4[CH:20]=[N:21][C:16]([C:15]([F:31])([F:14])[F:32])=[CH:17][CH:18]=4)=[CH:30][CH:29]=3)[CH2:25][CH2:26]2)(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

Conditions

Temperature: 80 °C

Procedure

1.18 g of commercially available 3-Chloro-4-cyano-benzenesulfonyl chloride were dissolved in 30 ml dichloromethane. Then 880 mg 5-(6-Trifluoromethyl-pyridin-3-yl)-2,3-dihydro-1H-indole were added followed by 15 ml pyridine and 407 mg 4-dimethylaminopyridine. The mixture was stirred at 80° C. for thirty minutes. The mixture was diluted with 100 ml of dichloromethane and washed with 100 ml water and 100 ml saturated NaHCO3 solution. The organic layer was then separated and dried over MgSO4. The solvent was removed in vacuo to obtain 1.49 g 2-Chloro-4-[5-(6-trifluoromethyl-pyridin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile.

Workup

washwashed with 100 ml water and 100 ml saturated NaHCO3 solution
customThe organic layer was then separated
dry with materialdried over MgSO4
customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-ea17378f5c384d2e862078a41f1f99ae
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329725B2

Reaction notes

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