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

HRID 1801461Notes

Reaction equation

HRID 1801461 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]=[CH:21][C:18]([CH2:19]Cl)=[CH:17][CH:16]=1.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]([CH2:19][C:18]3[CH:21]=[CH:22][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)[C:10]=2[N:11]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 218737726-Bromo-2H-pyrido[3,2-B][1,4]oxazin-3(4H)-one

Product 1

HCID 866493756-bromo-4-(4-methoxy-benzyl)-4H-pyrido[3,2-b][1,4]oxazin-3-oneYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 6-bromo-2H-pyrido[3,2-b]-1,4-oxazin-3(4H)-one (2.0 g; prepared according to WO 01/30782) in DMF (40 mL) was treated with 4-methoxybenzyl chloride (1.18 mL) and Cs2CO3 (8.5 g) and stirred at rt for 2 h. The solvent was evaporated under reduced pressure and the residue was partitioned between EA and water. The org. layer was washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue was triturated with Hept, affording a beige solid (2.8 g, 92% yield).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was partitioned between EA and water
  3. washlayer was washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with Hept

Sources & evidence

ORD record
ord-ed5b84a400c54633863e7ad3745ac3d5
Source dataset
uspto-grants-2013_01
Patent number
US08349826B2

Reaction notes

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