Water → 1,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 63273

反応式

HRID 63273 の反応式
Br[C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:42]=[CH:41][C:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][CH2:33][C:27]=3[CH:26]=2)O1.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCOCC1.O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].C(OCC)(=O)C>[CH3:16][C:14]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:9][O:8][C:7]2[C:2]([C:25]3[CH:42]=[CH:41][C:28]4[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:38])([CH3:39])[CH3:40])=[O:35])[CH2:32][CH2:33][C:27]=4[CH:26]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=1

参加物

9

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 57505869tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylateHCID 866705442-Bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine

生成物 1

HCID 706652431,1-dimethylethyl 7-(3-{[(4-methyl-2-pyridinyl)methyl]oxy}-2-pyridinyl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

試薬・触媒・溶媒 4

HCID 24290Palladium Chloride触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 8857Ethyl Acetate溶媒HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
120 °C

実験手順

To a degassed mixture of 2-bromo-3-{[(4-methyl-2-pyridinyl)methyl]oxy}pyridine (2.83 g), 1,1-dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (4.54 g) and cesium carbonate (9.9 g) in dioxane:water (4:1, 40 ml) was added PdCl2.dppf (0.828 g). The reaction mixture was heated at 120° C. overnight. The reaction mixture was added to water and extraction was carried out with ethyl acetate. The organic layer was dried over sodium sulphate and the filtrate was concentrated in vacuo. The crude product was purified through silica, eluting with 0-40% ethyl acetate in hexane. Appropriate fractions were concentrated in vacuo to yield the title compound, 3.8 g (84%).

後処理

  1. dry with materialThe organic layer was dried over sodium sulphate
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified through silica
  4. washeluting with 0-40% ethyl acetate in hexane
  5. concentrationAppropriate fractions were concentrated in vacuo

出典と根拠

ORDレコード
ord-6b515ef1666142fa88156e73db3e63be
出典データセット
uspto-grants-2016_09
特許番号
US09447074B2

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