1-Fluoro-4-(methylsulphonyl)benzene → 2-Difluoromethyl-4-(4-methanesulfonyl-phenoxy)-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 1643704Notes

Reaction equation

HRID 1643704 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:12][N:13]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[CH:32]=[C:31]([OH:33])[C:24]3[CH2:25][CH:26]([CH:28]([F:30])[F:29])[O:27][C:23]=3[CH:22]=2)=[O:20])=[N:14]1>>[CH3:12][N:13]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([C:21]2[CH:32]=[C:31]([O:33][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:24]3[CH2:25][CH:26]([CH:28]([F:30])[F:29])[O:27][C:23]=3[CH:22]=2)=[O:20])=[N:14]1

Participants

3

Reactant 2

HCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 595604162-difluoromethyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Product 1

HCID 595598682-Difluoromethyl-4-(4-methanesulfonyl-phenoxy)-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Procedure

The title compound was prepared in a similar manner as described for Example 33, from 4-fluorophenyl methyl sulfone (28.2 mg, 0.162 mmol) and 2-difluoromethyl-4-hydroxy-2,3-dihydro-benzofuran-6-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide (223a) (50 mg, 0.160 mmol) to give a white solid (18 mg, 24% yield). 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 1 H) 7.85-8.02 (m, 2 H) 7.22-7.38 (m, 2 H) 7.02-7.21 (m, 3 H) 6.77 (d, J=2.02 Hz, 1 H) 5.94 (t, 1 H) 5.02 (br. s., 1 H) 3.78 (s, 3 H) 3.55-3.65 (m, 1 H) 3.23-3.33 (m, 1 H) 3.09 (s, 3 H); LCMS for C21H19F2N3O5S m/z 464.00 (M+H)+.

Sources & evidence

ORD record
ord-d7bb85d7b6eb4b2591292692566f2df0
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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