Cesium carbonate → HCID 117771380, compound

HRID 2201528Notes

Reaction equation

HRID 2201528 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[O:9])[C:5]([OH:19])=[CH:4][CH:3]=1.[C:20]([O-])([O-])=O.[Cs+].[Cs+].ClCI>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:19][CH2:20][N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=3)[C:8](=[O:9])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 117771679HCID 117771679, compound

Product 1

HCID 117771380HCID 117771380, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-bromo-N-(4-chlorobenzyl)-3-hydroxypicolinamide (200 mg, 0.59 mmol) and Cs2CO3 (516 mg, 2.93 mmol) in DMF (5 mL) was added chloroiodomethane (382 mg, 1.17 mmol) dropwise at 100° C. for 10 minutes. The mixture was concentrated in vacuo and the residue was suspended in water. The mixture was extracted with EtOAc and the organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the crude 6-bromo-3-(4-chlorobenzyl)-2H-pyrido[2,3-e][1,3]oxazin-4(3H)-one (150 mg, yield: 73%) without further purification. MS (M+H)+: 353/355.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bad35b9b3226455d9346074813c894b9
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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