5-Bromo-2-thiophenesulfonamide → 5-[8-Cyano-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-3-ylethynyl]-thiophene-2-sulfonic acid amide

HRID 1293945Notes

Reaction equation

HRID 1293945 reaction equation
[C:1]([C:3]1[N:7]2[CH:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:10]=[C:11]([C:12]#[N:13])[C:6]2=[N:5][CH:4]=1)#[CH:2].Br[C:25]1[S:29][C:28]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:27][CH:26]=1>>[C:12]([C:11]1[C:6]2[N:7]([C:3]([C:1]#[C:2][C:25]3[S:29][C:28]([S:30]([NH2:33])(=[O:32])=[O:31])=[CH:27][CH:26]=3)=[CH:4][N:5]=2)[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][CH:15]=2)[CH:10]=1)#[N:13]

Participants

3

Reactant 2

HCID 12413045-Bromo-2-thiophenesulfonamideHCID 866080963-Ethynyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-8-carbonitrile

Product 1

HCID 167384665-[8-Cyano-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridin-3-ylethynyl]-thiophene-2-sulfonic acid amide

Procedure

The title compound was prepared from 3-ethynyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine-8-carbonitrile (example C.23) (150 mg, 0.5 mmol) and commercially available 5-bromothiophene-2-sulfonamide (117 mg, 0.5 mmol) according to general procedure II. Obtained as an off-white solid (80 mg, 35%). MS (ISP) 473.1 [(M+H)+]; mp 267–269° C.

Sources & evidence

ORD record
ord-6afa6b3d9fa1495fb2c51a54534b80f1
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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