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

HRID 2100379Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 80 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-da98fca63daa45a9a96aef0ff084ae7f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572790B2

Reaction notes

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