(4-Methoxyphenyl)boronic acid → (+,-) Cis Propane-2-sulfonic Acid [2-(4'-methoxy-biphenyl-4-yl)-cyclopentyl)-amide

HRID 989513Notes

Reaction equation

HRID 989513 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.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([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][CH:23]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103291(+,-) Cis Propane-2-sulfonic Acid [2-(4'-methoxy-biphenyl-4-yl)-cyclopentyl)-amideYield 89.2%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (200 mg, 0.51 mmol, prepared in example 17) and 4-methoxyphenylboronic acid (93 mg, 0.61 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 170 mg (89%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-c3ba8c3067b14aad8fbf0e502d946bc3
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

Loading…