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

HRID 1510428노트

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HRID 1510428 반응식
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

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 533260944-Bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide

생성물 1

HCID 671211705-(4-Chlorophenyl)-N-cyclopentyl-4-cyclopropylisoxazole-3-carboxamide

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-63718b3ad9de48b2815293c5b3fde27b
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08211927B2

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