1-Difluoromethyl-3-methyl-1H-pyrazole-4-sulfonyl chloride → HCID 67244695, compound

HRID 2422874Notes

Reaction equation

HRID 2422874 reaction equation
[F:1][CH:2]([F:13])[N:3]1[CH:7]=[C:6]([S:8](Cl)(=[O:10])=[O:9])[C:5]([CH3:12])=[N:4]1.[F:14][C:15]([F:33])([F:32])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([C@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=1>>[F:14][C:15]([F:32])([F:33])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([C@H:29]([NH:31][S:8]([C:6]2[C:5]([CH3:12])=[N:4][N:3]([CH:2]([F:13])[F:1])[CH:7]=2)(=[O:10])=[O:9])[CH3:30])=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 64854221-Difluoromethyl-3-methyl-1H-pyrazole-4-sulfonyl chlorideHCID 67243618HCID 67243618, compound

Product 1

HCID 67244695HCID 67244695, compound

Procedure

Palladium acetate (34 mg, 0.150 mmol) was added to a mixture of 2-(trifluoromethoxy)phenylboronic acid (773 mg, 3.75 mmol) and (R)-(+)-1-(4-bromophenyl)ethylamine (300 mg, 1.50 mmol) in water (12 ml). This mixture was heated in a microwave oven at 150° C. for 10 min, then diluted with methanol (200 ml) and purified on a SCX column (eluted with 2M ammonia in methanol) to give (R)-1-(2′-trifluoromethoxy-biphenyl-4-yl)-ethylamine (345 mg, 1.23 mmol, 81.9%) as a gum. The title compound was then prepared in a similar manner to (R)-2,5-dimethyl-furan-3-sulfonic acid [1-(5′-fluoro-2′-methoxy-biphenyl-4-yl)-ethyl]-amide (Example 10) using 1-difluoromethyl-3-methylpyrazole-4-sulfonyl chloride and (R)-1-(2′-trifluoromethoxy-biphenyl-4-yl)-ethylamine. Title compound: 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1H), 7.42-7.16 (m, 8H), 6.97 (s, 1H), 4.88 (d, 1H), 4.52 (m, 1H), 2.30 (s, 3H), 1.56 (d, 3H) ppm; MS (ESI) m/z: 476 [M+H]+.

Sources & evidence

ORD record
ord-84c927e3f6d24af685ab1bf3c6d071ff
Source dataset
uspto-grants-2011_06
Patent number
US07960365B2

Reaction notes

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