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

반응식

HRID 63273 반응식
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

참가 물질

9

반응물 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

생성물 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

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 8857Ethyl Acetate용매HCID 218864351,4-Dioxane--water (1/1)용매

반응 조건

온도
120 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-6b515ef1666142fa88156e73db3e63be
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447074B2

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