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

HRID 989515Notes

Reaction equation

HRID 989515 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]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[F:20][C:21]([F:32])([F:33])[O:22][C:23]1[CH:28]=[CH:27][C:26]([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:25][CH:24]=1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 69113142(+,-) Cis Propane-2-sulfonic Acid [2-(4'-trifluoromethoxy-biphenyl-4-yl)-cyclopentyl]-amideYield 44%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (203 mg, 0.52 mmol, prepared in example 17) and 4-trifluoromethoxyphenylboronic acid (128 mg, 0.62 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, followed by a second chromatography eluting with 0.2% MeOH/methylene chloride to afford 97 mg (44%) of the title compound.

Workup

  1. customPurification by silica chromatography
  2. washwas achieved eluting with methylene chloride
  3. washeluting with 0.2% MeOH/methylene chloride

Sources & evidence

ORD record
ord-bf9c8ce19505473cacafc7e623bcd661
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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