Iodoethane → 6-bromo-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509337ノート

反応式

HRID 1509337 の反応式
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1.I[CH2:20][CH3:21].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]([CH2:20][CH3:21])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1

参加物

6

反応物 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

生成物 1

HCID 866836836-bromo-1-ethyl-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one収率 48.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
50 °C

実験手順

In a 15 mL reaction tube was added 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (300 mg, 0.983 mmol), iodoethane (0.095 mL, 1.180 mmol) and potassium carbonate (408 mg, 2.95 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give a brown suspension. This was stirred at 50° C. under a nitrogen atmosphere for 60 minutes. The reaction mixture was diluted with saturated sodium bicarbonate solution (5 mL) and extracted into ethyl acetate (3×5 mL). The combined organic phases were washed with 50:50 water:brine (3×5 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a brown solid. This was purified by Biotage chromatography (25 g silica cartridge, cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80) to give the title compound as a beige solid (160 mg, 48.8% yield).

後処理

  1. customIn a 15 mL reaction tube
  2. customto give a brown suspension
  3. extractionextracted into ethyl acetate (3×5 mL)
  4. washThe combined organic phases were washed with 50:50 water
  5. dry with materialbrine (3×5 mL), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto give a brown solid
  9. customThis was purified by Biotage chromatography (25 g silica cartridge, cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80)

出典と根拠

ORDレコード
ord-d1392d180a61491c8ca27fc84f24db54
出典データセット
uspto-grants-2015_12
特許番号
US09221838B2

反応ノート

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