Potassium Carbonate → HCID 86727382, compound

HRID 519023Notes

Reaction equation

HRID 519023 reaction equation
[C:1]([C:4]1[C:14]([F:15])=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CC(C)=O>[C:1]([C:4]1[C:14]([F:15])=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[N:11]([CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 86727383HCID 86727383, compound

Product 1

HCID 86727382HCID 86727382, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-acetyl-7-fluoro-2H-benzo[b][1,4]oxazin-3(4H)-one (12 g, 57.4 mmol) and K2CO3 (11.89 g, 86 mmol) in acetone (120 mL) was added ethyl 2-bromopropanoate (23.6 mL, 172 mmol) and the mixture was stirred and heated at 80° C. for 16 h. The mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluting with 5-10% EtOAc in petroleum ether) to give ethyl 2-(6-acetyl-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate as a gray solid (13.2 g, 74.4%). 1H-NMR (CDCl3, 400 MHz): δ 7.40 (d, J=6.4 Hz, 1H), 6.80 (d, J=10.8 Hz, 1H), 5.24 (q, J=11.2 Hz, 1H), 4.66 (q, J=15.2 Hz, 2H), 4.23 (m, 2H), 2.60 (d, J=5.2 Hz, 3H), 1.63 (d, J=7.2 Hz, 3H), 1.23 (t, 3H).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solvent was removed in vacuo
  3. customThe residue was purified by column chromatography on silica gel (eluting with 5-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-88cf4b541e7b405db652c8152544067d
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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