Potassium Phosphate, Tribasic → 5-(4-Chlorophenyl)-N-cyclopentyl-4-cyclopropylisoxazole-3-carboxamide

HRID 1510428Notes

Reaction equation

Br[C:2]1[C:3]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[CH:22]1(B(O)O)[CH2:24][CH2:23]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[O:5][N:4]=[C:3]([C:14]([NH:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])[C:2]=2[CH:22]2[CH2:24][CH2:23]2)=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide (40 mg, 0.11 mmol), cyclopropylboronic acid (22 mg, 0.26 mmol), and tricyclohexylphosphine (6 mg, 0.02 mmol) in toluene (1 mL) was degassed with Argon. 2M aqueous potassium phosphate (0.35 mL, 0.7 mmol) and palladium(II) acetate were added and the reaction heated to 100° C. for 3 hours. The volatiles were removed in vacuo and compound was purified by silica gel chromatography eluting with 2% methanol in dichloromethane to afford the title compound: (6.8 mg, 0.02 mmol). MS (ESI) m/z (M+H+): 331.2

Workup

customwas degassed with Argon
customThe volatiles were removed in vacuo and compound
customwas purified by silica gel chromatography
washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record: ord-63718b3ad9de48b2815293c5b3fde27b
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211927B2

Reaction notes

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