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

HRID 495421

反応式

HRID 495421 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9abeb718c33d4565b68635db0f5750c3
出典データセット
uspto-grants-2005_09
特許番号
US06939871B2

関連ノート

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