Potassium Carbonate → (+,-) Cis Propane-2-sulfonic Acid [2-(3'-methanesulfonylamino-biphenyl-4-yl)-cyclopentyl]-amide

HRID 989503Notes

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.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:31]=[CH:32][CH:33]=2)O1.C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:38][S:35]([NH:34][C:30]1[CH:31]=[C:32]([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:33]=[CH:28][CH:29]=1)(=[O:37])=[O:36]

Participants

Conditions

Temperature: 90 °C

Procedure

(+,−) Cis propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (185 mg, 0.47 mmol, prepared in example 17) and N-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide (168 mg, 0.56 mmol) were dissolved in 25 mL of n-propanol and 78 mg (0.56 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (5 mg) and the mixture refluxed at 90° C. for 4 hours. The reaction is worked up in a manner analogous to example 3. Purification by silica chromatography using a Chromatotron® was achieved eluting with 99:1 methylene chloride:methanol to afford 135 mg (66%) of the title compound as a white solid. The NMR was consistent with the assigned structure.

Workup

customPurification by silica chromatography
washwas achieved eluting with 99:1 methylene chloride

Sources & evidence

ORD record: ord-5b6e2abd2a8c48d39423a91fe43edaeb
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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