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

HRID 989488Notes

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]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)#[N:21].C(=O)([O-])[O-].[K+].[K+]>C(O)CC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:20]([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)#[N:21]

Participants

Conditions

Temperature: 90 °C

Procedure

(+,−) Trans propane-2-sulfonic acid [2-(4-iodo-phenyl)-cyclopentyl]-amide (375 mg, 0.95 mmol, prepared in example 2) and 4-cyanophenylboronic acid (168 mg, 1.14 mmol) were dissolved in 20 mL of n-propanol and 25 mg (0.18 mmol)of potassium carbonate in 5 mL of water added. A catalytic amount of palladium acetate is added (11 mg) and the mixture refluxed at 90° C. for 7 hours. The reaction is worked up as in preparation 6. The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. Purification by silica chromatography using a Chromatotron® was achieved eluting with 99:1 methylene chloride:methanol to afford 307 mg (87%) of the title compound. The NMR was consistent with the assigned structure.

Workup

customThe reaction is worked up as in preparation 6
dry with materialThe combined organics were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification by silica chromatography
washwas achieved eluting with 99:1 methylene chloride

Sources & evidence

ORD record: ord-8a056dec58dc4e3b8e0282d027f213ff
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

Loading…