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

HRID 2100379노트

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HRID 2100379 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-da98fca63daa45a9a96aef0ff084ae7f
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572790B2

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