Methyl bromoacetate → 7-Bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 473949Notes

Reaction equation

N12CCCN=C1CC[CH2:4][CH2:3][CH2:2]2.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[OH:20].BrCC(OC)=[O:24]>CN1CCCC1=O.C(OCC)(=O)C>[Br:19][C:16]1[CH:17]=[CH:18][C:13]2[NH:12][C:2](=[O:24])[CH:3]([CH3:4])[O:20][C:14]=2[CH:15]=1

Participants

Conditions

Temperature: 180 °C

Procedure

1,8-Diazabicyclo[5.4.0]undec-7-ene (145.0 μL, 0.975 mmol) was added at room temperature to a solution of 2-amino-5-bromophenol A-1 (200.0 mg, 1.064 mmol) and methyl 2-bromoacetate (115.0 μL, 0.886 mmol) in anhydrous 1-methylpyrrolidin-2-one (4.20 mL) under an atmosphere of argon, in a 10 mL microwave reactor vial. The sealed reaction mixture was heated at 180° C. for 3 mins under microwave irradiation and then diluted with ethyl acetate (25 mL). The organic layer was washed with brine (3×20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give 7-bromo-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one A-2 (217.0 mg, Yield=100%). MS (ESI) [M+1]+ 242, 244.

Workup

customThe sealed reaction mixture
washThe organic layer was washed with brine (3×20 mL)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure
customThe crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient)

Sources & evidence

ORD record: ord-6f4d9b8365574877b39e36a9f07f2898
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637507B2

Reaction notes

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