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

HRID 517963ノート

反応式

HRID 517963 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-08b053b5c8524fb0809a3c55e55fa61f
出典データセット
uspto-grants-2015_08
特許番号
US09115126B2

反応ノート

読み込み中…