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

HRID 1510428ノート

反応式

HRID 1510428 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-63718b3ad9de48b2815293c5b3fde27b
出典データセット
uspto-grants-2012_07
特許番号
US08211927B2

反応ノート

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