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

HRID 989511Notes

Reaction equation

HRID 989511 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 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103249(+,-) Cis Propane-2-sulfonic Acid [2-(2',4'-difluoro-biphenyl-4-yl)-cyclopentyl]-amideYield 31%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (710 mg, 1.81 mmol, prepared in example 17) and 2,4-difluorophenylboronic acid (285 mg, 1.81 mmol) was accomplished in a manner analogous to that 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. Further purification was achieved by reverse phase C18 chromatography to afford 213 mg (31%) of the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-f3343884b7c64cd0ab69a37d02a1a920
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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