Phenylboronic Acid → HCID 59103244, compound

HRID 989517Notes

Reaction equation

HRID 989517 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.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[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 66827Phenylboronic AcidHCID 10000637(R,R) Propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide

Product 1

HCID 59103244HCID 59103244, compoundYield 53%

Procedure

The Suzuki coupling of (+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (167 mg, 0.43 mmol, prepared in example 17) and phenylboronic acid (62 mg, 0.51 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. Further purification was achieved by reverse phase C18 chromatography to afford 77 mg (53%) of the title compound as a solid.

Workup

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

Sources & evidence

ORD record
ord-2af9d8dada1e46169c8af843be4a8157
Source dataset
uspto-grants-2003_10
Patent number
US06639107B1

Reaction notes

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