3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 57901670, compound

HRID 1851577Notes

Reaction equation

HRID 1851577 reaction equation
[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:15].[F:16][C:17]([F:29])([F:28])[C:18]1[CH:19]=[C:20]([S:24](Cl)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1>N1C=CC=CC=1>[S:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[N:15]([S:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:28])[F:29])[CH:19]=1)(=[O:26])=[O:25])[S:24]([C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:29])([F:28])[F:16])[CH:19]=1)(=[O:26])=[O:25]

Participants

4

Reactant 2

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chlorideHCID 579017772-(4,5-Dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine

Product 1

HCID 57901670HCID 57901670, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 2-(4,5-dihydro-1,3-thiazol-2-yl)-1H-indole-7-amine (100 mg) and pyridine (3 mL) was added 3-(trifluoromethyl)benzenesulfonyl chloride (140 mg) at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (93 mg, yield 32%) as pale-yellow crystals. M+1=634.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-115277aaa9f344b0bd7547a7dfad44c1
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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