Pyridine → 2-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one

HRID 60377ノート

反応式

HRID 60377 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][NH:12][C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH:18]1([C:21]2[N:22]=[C:23]3[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][N:24]3[C:32]=2[CH3:33])[CH2:20][CH2:19]1.N1C=CC=CC=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:16][C:15]3[CH:14]=[CH:13][N:12]([C:26]4[CH:27]=[CH:28][C:23]5[N:24]([C:32]([CH3:33])=[C:21]([CH:18]6[CH2:20][CH2:19]6)[N:22]=5)[CH:25]=4)[C:11](=[O:17])[C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 580155582-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-oneHCID 89690439HCID 89690439、化合物

生成物 1

HCID 718165182-(4-Chlorophenyl)-5-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)furo[3,2-c]pyridin-4(5H)-one収率 5.9%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-(4-chlorophenyl)furo[3,2-c]pyridin-4(5H)-one (100 mg), (2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)boronic acid (106 mg), copper(II) acetate (4.99 mg), pyridine (0.066 mL), MS-4A (48.9 mg) and DMF (5.0 mL) was stirred at room temperature for 4 hr and at 50° C. overnight. After filtration of the obtained mixture through Celite, the filtrate was poured into 1 N hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained solid was washed with ethanol to give the title compound (10.0 mg) as a pale brown solid.

後処理

  1. filtrationAfter filtration of the obtained mixture through Celite
  2. additionthe filtrate was poured into 1 N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe obtained solid was washed with ethanol

出典と根拠

ORDレコード
ord-2034a445db9f4e60aba5da68a027397c
出典データセット
uspto-grants-2016_09
特許番号
US09440987B2

反応ノート

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