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

HRID 896088

반응식

HRID 896088 반응식
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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 81531Diisopropylethylamine용매

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-aa4313d367454407a66153bd4db34413
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919336B2

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