Cesium carbonate → (S)-1-{2-Chloro-6-[1-(4-fluorophenyl)ethylamino]pyridin-4-yl}ethanone

HRID 1187745ノート

反応式

HRID 1187745 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[C:4]([Cl:11])[N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]([NH2:21])[CH3:20])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:11][C:4]1[CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([NH:21][C@H:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH3:20])[N:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 2779063(S)-1-(4-Fluorophenyl)-ethylamineHCID 221194461-(2,6-Dichloropyridin-4-YL)ethanone

生成物 1

HCID 86659408(S)-1-{2-Chloro-6-[1-(4-fluorophenyl)ethylamino]pyridin-4-yl}ethanone収率 16%

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

535 mg of 1-(2,6-dichloropyridin-4-yl)ethanone (Steps 1 and 2 of Example 29), 391 mg of (S)-(−)-1-(4-fluorophenyl)ethylamine, 262 mg of (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1.28 g of cesium carbonate and 63 mg of palladium acetate were added in turn to 10 ml of degassed toluene, and the mixture was stirred at 100° C. for 3 hours under argon atmosphere. The reaction solution was purified by silica gel column chromatography to obtain 132 mg of the objective compound as pale yellow powder.

後処理

  1. customThe reaction solution was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fbe9be99735845158f753ad84bf7e346
出典データセット
uspto-grants-2014_03
特許番号
US08673891B2

反応ノート

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