1,4-Dioxane → 3-Amino-4-(methylamino)-6-(4-(pyridin-2-ylmethoxy)-3-(trifluoromethyl)phenyl)picolinonitrile

HRID 517963노트

반응식

HRID 517963 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[C:11]([C:23]([F:26])([F:25])[F:24])[CH:10]=2)O1.[NH2:28][C:29]1[C:30]([C:38]#[N:39])=[N:31][C:32](Cl)=[CH:33][C:34]=1[NH:35][CH3:36].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.O1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[NH2:28][C:29]1[C:30]([C:38]#[N:39])=[N:31][C:32]([C:9]2[CH:22]=[CH:21][C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[C:11]([C:23]([F:24])([F:25])[F:26])[CH:10]=2)=[CH:33][C:34]=1[NH:35][CH3:36]

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 75806TricyclohexylphosphineHCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileHCID 672941632-((4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)methyl)pyridine

생성물 1

HCID 672942713-Amino-4-(methylamino)-6-(4-(pyridin-2-ylmethoxy)-3-(trifluoromethyl)phenyl)picolinonitrile

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매

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온도
100 °C

실험 절차

The mixture of 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenoxy)methyl)pyridine (1.35 g), 3-amino-6-chloro-4-(methylamino)-picolinonitrile (0.5 g), tris(dibenzylideneacetone)dipalladium (125 mg), tricyclohexylphosphine (92 mg) in a mixed solvent of dioxane (15 ml) and water (10 ml) was heated under nitrogen at 100° C. for 3 hours. After cooling to room temperature, the mixture extracted with ethyl acetate (200 ml), organic layer dried over sodium sulphate, solvent removed under reduced pressure, residue was used for next step without further purification. MS m/z 400 (M+H).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture extracted with ethyl acetate (200 ml), organic layer
  3. dry with materialdried over sodium sulphate, solvent
  4. customremoved under reduced pressure, residue
  5. customwas used for next step without further purification

출처 및 근거

ORD 기록
ord-08b053b5c8524fb0809a3c55e55fa61f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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