Cesium carbonate → HCID 117801547, compound

HRID 2201522Notes

Reaction equation

HRID 2201522 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]([F: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]([F:18])=[CH:14][CH:13]=3)[C:8](=[O:9])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11644ChloroiodomethaneHCID 117771602HCID 117771602, compound

Product 1

HCID 117801547HCID 117801547, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-N-(4-fluorobenzyl)-3-hydroxypicolinamide (100 mg, 0.31 mmol) and Cs2CO3 (219 mg, 0.62 mmol) in DMF (10 mL) was added chloroiodomethane (87 mg, 0.46 mmol) dropwise at 110° C. under N2. The mixture was stirred at 110° C. for 0.5 hour. Then the mixture was concentrated and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by prep-TLC (PE:EtOAc=2:1) to afford the product of 6-bromo-3-(4-fluorobenzyl)-2H-pyrido[2,3-e][1,3]oxazin-4(3H)-one (70 mg, yield: 67.3%). 1H-NMR (CDCl3, 400 MHz) δ 7.46˜7.48 (m, 1H), 7.26˜7.29 (m, 2H), 7.18˜7.20 (m, 1H), 6.96 (t, J=8.4 Hz, 2H), 5.16 (s, 2H), 4.70 (s, 2H). MS (M+H)+: 337/339.

Workup

  1. concentrationThen the mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by prep-TLC (PE:EtOAc=2:1)

Sources & evidence

ORD record
ord-435d099e37644c30813c974200bc27ac
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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