Cesium carbonate → [5-(3-Amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

HRID 896088

反応式

HRID 896088 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[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.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:33][C:34]([NH2:38])([CH3:37])[C:35]#[CH:36]>C(N(C(C)C)CC)(C)C.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.[Cu]I>[NH2:38][C:34]([CH3:37])([CH3:33])[C:35]#[C:36][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[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

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 763193-Butyn-2-amine, 2-methyl-HCID 22349594(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

生成物 1

HCID 10180494[5-(3-Amino-3-methyl-but-1-ynyl)-2-methoxy-phenyl]-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 81531Diisopropylethylamine溶媒

実験手順

(5-Bromo-2-methoxy-phenyl)-[6-(2,4-difluoro-phenylamino)-pyridin-3-yl]-methanone (1.36 g; 3.2 mmol) is dissolved in hot diisopropylethylamine (120 ml). PdCl2(PPh3)2 (680 mg; 0.97 mmol), Cs2CO3 (6.8 g; 0.02 mmol), CuI (0.68 g; 3.57 mmol) and 1,1-dimethyl-prop-2-ynylamine (6.8 ml; 65 mmol) are added and the mixture refluxed under argon for 30 min. The reaction mixture is decanted from the solid, evaporated, taken up in water and extracted three times with ethyl acetate. The combined organic phases are dried over Na2SO4 and evaporated to dryness. Purification via chromatography (SiO2; toluene/ethanol/NH3conc 96/4/0.2>94/6/0.3) yields the title compound as a slightly colored foam (1.14 g; 84%).

後処理

  1. temperaturethe mixture refluxed under argon for 30 min
  2. customThe reaction mixture is decanted from the solid
  3. customevaporated
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases are dried over Na2SO4
  6. customevaporated to dryness
  7. customPurification via chromatography (SiO2; toluene/ethanol/NH3conc 96/4/0.2>94/6/0.3)

出典と根拠

ORDレコード
ord-aa4313d367454407a66153bd4db34413
出典データセット
uspto-grants-2005_07
特許番号
US06919336B2

関連ノート

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