2,4-Difluorophenylboronic acid → (+,-) Trans Propane-2-sulfonic Acid [2-(2',4'-difluoro-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989491Notes

Reaction equation

HRID 989491 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1B(O)O>>[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 27343342,4-Difluorophenylboronic acidHCID 11784171(+,-) Trans Propane-2-sulfonic Acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103293(+,-) Trans Propane-2-sulfonic Acid [2-(2',4'-difluoro-biphenyl-4-yl)-cyclopentyl]-amideYield 89%

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (120 mg, 0.31 mmol, prepared in example 2) and 2,4-difluorophenylboronic acid (60 mg, 0.38 mmol) were treated as described in example 6 to afford 103 mg (89%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Sources & evidence

ORD record
ord-c6eadc01607e49c8bddd086f53cac05a
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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