Sodium hydride → Methyl 4bromo-3{[2-(4-morpholinyl)-2-oxoethyl]oxy}benzoate

HRID 2100379ノート

反応式

HRID 2100379 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].Br[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 6425184Methyl 4-Bromo-3-hydroxybenzoateHCID 139968762-Bromo-1-(morpholin-4-yl)ethan-1-one

生成物 1

HCID 68834044Methyl 4bromo-3{[2-(4-morpholinyl)-2-oxoethyl]oxy}benzoate収率 14.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl 4-bromo-3-hydroxybenzoate (71 mg) and 4-(bromoacetyl)morpholine (71 mg) were combined in DMF (5 ml). Sodium hydride (14 mg, 60% dispersion in mineral oil) was added and the reaction heated at 80° C. under nitrogen for 16 hours. The reaction was quenched with water (2 ml) and solvent the evaporated in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate/chloroform (1:1, 2×10 ml). The organic layers were combined, dried using a hydrophobic filter and evaporated under vacuum. The residue was partially purified by SPE (2 g, Si), eluting with a methanol/chloroform gradient (0.5% to 5%), and the product fractions further purified by mdap, to give methyl 4bromo-3{[2-(4-morpholinyl)-2-oxoethyl]oxy}benzoate as a white solid (16 mg).

後処理

  1. customThe reaction was quenched with water (2 ml) and solvent the
  2. customevaporated in vacuo
  3. customThe residue was partitioned between water (10 ml) and ethyl acetate/chloroform (1:1, 2×10 ml)
  4. customdried
  5. filtrationa hydrophobic filter
  6. customevaporated under vacuum
  7. customThe residue was partially purified by SPE (2 g, Si)
  8. washeluting with a methanol/chloroform gradient (0.5% to 5%)
  9. customthe product fractions further purified by mdap

出典と根拠

ORDレコード
ord-da98fca63daa45a9a96aef0ff084ae7f
出典データセット
uspto-grants-2009_08
特許番号
US07572790B2

反応ノート

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