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

HRID 896091노트

반응식

HRID 896091 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매2회HCID 178418476HCID 178418476, 화합물촉매2회HCID 8471Triethylamine용매

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ba33644dc0524c5699d2ada5985d8904
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919336B2

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