3-Butyn-2-amine, 2-methyl- → (5-Bromo-2-chloro-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanol

HRID 896091ノート

反応式

HRID 896091 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:14][CH:15]=2)=[O:9])[CH:7]=1.NC(C)(C)C#C>CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:25])=[C:6]([CH:8]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])=[CH:14][CH:15]=2)[OH:9])[CH:7]=1

参加物

6

反応物 2

HCID 763193-Butyn-2-amine, 2-methyl-2 回HCID 22349591(5-Bromo-2-chloro-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

生成物 1

HCID 22349578(5-Bromo-2-chloro-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanol

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒2 回HCID 178418476HCID 178418476、化合物触媒2 回HCID 8471Triethylamine溶媒

実験手順

(5-Bromo-2-chloro-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone (1.5 g; 3.5 mmol) is dissolved in NEt3 (110 ml), 3-amino-3-methyl-1-butyne (1.7 ml; 15.9 mmol), CuI (200 mg; 1 mmol), PdCl2(PPh3)2 (250 mg; 0.35 mmol) added and refluxed for 45 min. Since only small amount of product is formed, more PdCl2(PPh3)2 (500 mg; 0.7 mmol), CuI (500 mg; 2.5 mmol) and 3-amino-3-methyl-1-butyne (2 ml; 18.7 mmol) is added and refluxing continued for 2.5 hours. The reaction mixture is decanted, the solvent evaporated and the residue purified by chromatography (SiO2; toluene/ethanol/NH3conc 95/5/0.2) to yield the title compound as slightly colored foam (730 mg; 48%).

後処理

  1. temperaturerefluxed for 45 min
  2. customSince only small amount of product is formed
  3. temperaturerefluxing
  4. customThe reaction mixture is decanted
  5. customthe solvent evaporated
  6. customthe residue purified by chromatography (SiO2; toluene/ethanol/NH3conc 95/5/0.2)

出典と根拠

ORDレコード
ord-ba33644dc0524c5699d2ada5985d8904
出典データセット
uspto-grants-2005_07
特許番号
US06919336B2

反応ノート

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