Sodium Carbonate → 1,1-dimethylethyl 7-{5-acetyl-2-[(2-pyrazinylmethyl)oxy]phenyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate

HRID 63275

반응식

HRID 63275 반응식
Br[C:2]1[CH:3]=[C:4]([C:16](=[O:18])[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1.CC1(C)C(C)(C)OB([C:27]2[CH:44]=[CH:43][C:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35][C:29]=3[CH:28]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[C:16]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:15]=[N:14][CH:13]=[CH:12][N:11]=2)=[C:2]([C:27]2[CH:44]=[CH:43][C:30]3[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])[CH2:34][CH2:35][C:29]=3[CH:28]=2)[CH:3]=1)(=[O:18])[CH3:17]

참가 물질

5

반응물 3

HCID 10340Sodium 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 706653921-{3-Bromo-4-[(2-pyrazinylmethyl)oxy]phenyl}ethanone

생성물 1

HCID 706651151,1-dimethylethyl 7-{5-acetyl-2-[(2-pyrazinylmethyl)oxy]phenyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate수율 30%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a stirred solution of 1-{3-bromo-4-[(2-pyrazinylmethyl)oxy]phenyl}ethanone (0.2 g) and 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 (0.34 g) in DME (4 ml) was added aqueous sodium carbonate (2M, 0.98 ml). This was degassed with nitrogen for 15 min before adding Tetrakis (37 mg). The reaction was heated under reflux overnight. TLC indicated the reaction had gone to completion and so it was cooled, diluted with water and extracted with ethyl acetate. The combined organics were dried over sodium sulphate and concentrated in vacuo to yield a crude product which was purified by column chromatography, eluting with 0-18% ethyl acetate in hexane. The appropriate fractions were concentrated in vacuo to yield the title compound, 0.093 g, 30% yield.

후처리

  1. customThis was degassed with nitrogen for 15 min
  2. additionbefore adding Tetrakis (37 mg)
  3. temperatureThe reaction was heated
  4. temperatureunder reflux overnight
  5. temperaturewas cooled
  6. additiondiluted with water
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organics were dried over sodium sulphate
  9. concentrationconcentrated in vacuo
  10. customto yield a crude product which
  11. customwas purified by column chromatography
  12. washeluting with 0-18% ethyl acetate in hexane
  13. concentrationThe appropriate fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-f8761a456176490789c00ea482cbd734
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447074B2

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