1,2-Dimethoxyethane → 6-(4-Pyridyl)-4H-benzo[1,4]oxazin-3-one

HRID 495421

반응식

HRID 495421 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.[N:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+].COCCOC>O>[N:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[CH:4][C:5]3[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=3[CH:12]=2)=[CH:15][CH:14]=1

참가 물질

6

반응물 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

생성물 1

HCID 223266866-(4-Pyridyl)-4H-benzo[1,4]oxazin-3-one수율 43%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-bromo-4H-benzo[1,4]oxazin-3-one [N. Mazharuddin et al., Indian J. Chem. 1969, 7, 658] (1.37 g. 6 mmol), pyridine-4-boronic acid (0.72 g, 6 mmol), sodium bicarbonate (1.51 g, 18 mmol), (tetrakis-triphenylphosphine)palladium (0) (348 mg, 0.3 mmol) in water (18 mL), and 1,2-dimethoxyethane (30 mL), was stirred at reflux under an argon atmosphere for 72 h. Reaction mixture was cooled and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and dried (Na2SO4) and evaporated in vacuo to give a brown solid which was purified by chromatography on silica gel (30 g) eluting with 0-5% MeOH in EtOAc to give the title compound (0.58 g, 43%) as a yellow solid.

후처리

  1. temperatureat reflux under an argon atmosphere for 72 h
  2. customReaction mixture
  3. temperaturewas cooled
  4. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customto give a brown solid which
  9. customwas purified by chromatography on silica gel (30 g)
  10. washeluting with 0-5% MeOH in EtOAc

출처 및 근거

ORD 기록
ord-9abeb718c33d4565b68635db0f5750c3
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06939871B2

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