Potassium Carbonate → 6-bromo-1-(2-fluoroethyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

HRID 1509320Notes

Reaction equation

HRID 1509320 reaction equation
[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[NH:10][C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1.[F:19][CH2:20][CH2:21]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][C:5]2[N:10]([CH2:21][CH2:20][F:19])[C:9](=[O:11])[CH2:8][O:7][C:6]=2[N:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69804Ethane, 1-fluoro-2-iodo-HCID 866836506-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one

Product 1

HCID 866836766-bromo-1-(2-fluoroethyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-oneYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromo-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-one (400 mg, 1.311 mmol), 1-fluoro-2-iodoethane (684 mg, 3.93 mmol) and potassium carbonate (544 mg, 3.93 mmol) in DMF (4 ml) was heated under stirring for 3 h. The reaction mixture was cooled down and diluted with water (20 ml), the resulted mixture was extracted with DCM (3×20 ml). The combined organic phase was washed with water, brine, dried over sodium sulfate, concentrated to give the crude material which was purified by column chromatography eluted with ethyl acetate/cyclohexane 0-40% to give product 0.21 g. 1H NMR (500 MHz, CDCl3): 7.39-7.48 (m, 5H), 4.89 (s, 2H), 4.77 (t, 1H), 4.67 (t, 1H), 4.21 (t, 1H), 4.16 (t, 1H), LCMS (Method D): RT=1.24 min, M+H+=353.0.

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled down
  3. extractionthe resulted mixture was extracted with DCM (3×20 ml)
  4. washThe combined organic phase was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give the crude material which
  8. customwas purified by column chromatography
  9. washeluted with ethyl acetate/cyclohexane 0-40%

Sources & evidence

ORD record
ord-433e6dee90dd4c76abe72896eaa60e97
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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