(3,5-Difluorophenyl)boronic acid → (+,-) Cis Propane-2-sulfonic Acid [2-(3',5'-difluoro-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989512Notes

Reaction equation

HRID 989512 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:22]=[C:23](B(O)O)[CH:24]=[C:25]([F:27])[CH:26]=1>>[F:20][C:21]1[CH:22]=[C:23]([C:2]2[CH:7]=[CH:6][C:5]([C@H:8]3[CH2:12][CH2:11][CH2:10][C@H:9]3[NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:4][CH:3]=2)[CH:24]=[C:25]([F:27])[CH:26]=1

Participants

3

Reactant 2

HCID 2734338(3,5-Difluorophenyl)boronic acidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103253(+,-) Cis Propane-2-sulfonic Acid [2-(3',5'-difluoro-biphenyl-4-yl)-cyclopentyl]-amideYield 51%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (225 mg, 0.57 mmol, prepared in example 17) and 3,5-difluorophenylboronic acid (108 mg, 0.69 mmol) was accomplished in a manner analogous to the procedure described in example 27. The reaction was worked up in a manner analogous to example 3. Purification by silica chromatography using a Chromatotron® was achieved eluting with methylene chloride to afford 110 mg (51%) of the title compound as a colorless oil.

Workup

  1. customPurification by silica chromatography
  2. washwas achieved eluting with methylene chloride

Sources & evidence

ORD record
ord-6ebce68dca3141ae9bd3c5d2118a44aa
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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