Cesium carbonate → 6-bromo-4-(2,4-dimethoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-one

HRID 1640549Notes

Reaction equation

HRID 1640549 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[NH:9][C:10]=2[N:11]=1.[CH3:13][O:14][C:15]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:16]=1[CH2:17]Cl.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:6][CH2:7][C:8](=[O:12])[N:9]([CH2:17][C:16]3[CH:19]=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=3[O:14][CH3:13])[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 185052611-(Chloromethyl)-2,4-dimethoxybenzeneHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

Product 1

HCID 866420676-bromo-4-(2,4-dimethoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-bromo-4H-pyrido[3,2-b][1,4]oxazin-3-one (0.412 g, 1.8 mmol) and 2,4-dimethoxybenzyl chloride (0.336 g, 1.8 mmol; freshly prepared according to U.S. Pat. No. 5,817,653) in DMF (5 mL) was treated with Cs2CO3 (1.76 g, 3 eq.). The mixture was stirred at rt for 2 h, partitioned between EA and water. The aq. phase was extracted with EA and the combined org. layers washed with water, and brine, dried over MgSO4 and concentrated. The residue was purified by FC (Hept/EA 1:1) to give the title intermediate as a colourless oil (0.61 g, 90% yield).

Workup

  1. customfreshly prepared
  2. custompartitioned between EA and water
  3. extractionThe aq. phase was extracted with EA
  4. washlayers washed with water, and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by FC (Hept/EA 1:1)

Sources & evidence

ORD record
ord-9693bf2b05ea497a970b91d225c64443
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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