Dimethylformamide → 7-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,4-dihydro-2H-pyrido[2,3-b]pyrazin-3-one

HRID 659598Notes

Reaction equation

HRID 659598 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=C[CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][NH:5]2.[H-].[Na+].[Cl:15][C:16]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:17]=1[CH2:18]Br.C[N:27](C=O)C>>[Br:1][C:2]1[CH:11]=[N:27][C:9]2[NH:8][C:7](=[O:12])[CH2:6][N:5]([CH2:18][C:17]3[C:20]([F:25])=[CH:21][CH:22]=[C:23]([F:24])[C:16]=3[Cl:15])[C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27735492-(Bromomethyl)-3-chloro-1,4-difluorobenzeneHCID 669113076-Bromo-1,2,3,4-tetrahydroquinoxalin-2-one

Product 1

HCID 578858627-Bromo-1-(2-chloro-3,6-difluorobenzyl)-1,4-dihydro-2H-pyrido[2,3-b]pyrazin-3-oneYield 71%

Procedure

To a solution of 6-bromo-3,4-dihydro-1H-quinoxalin-2-one (228 mg, 1.00 mmol) in DMF (10 mL) was added NaH (40 mg of a 60% dispersion in mineral oil, 1.00 mmol) and the resulting mixture sonicated for 5 minutes. After stirring at room temperature for 20 minutes, 2-chloro-3,6-difluorobenzylbromide (242 mg, 1.00 mmol) was added and the mixture was stirred for 20 minutes. Solvent was reduced 90% and the residue was triturated with ether (3×1 mL) and water (2×2 mL) to give the title compound (275 mg, 71%). m.p. 214-216° C. (dec); LCMS: m/z=388/390/392 (M+H+); 1H-NMR (DMSO-d6, 400 MHz) δ 7.73 (s, 1H), 7.47-7.42 (m, 1H), 7.35 (s, 1H), 7.32-7.26 (m, 1H), 7.11 (s, 1H), 5.24, (s, 2H), 4.01 (s, 2H).

Workup

  1. customsonicated for 5 minutes
  2. stirringthe mixture was stirred for 20 minutes
  3. customthe residue was triturated with ether (3×1 mL) and water (2×2 mL)

Sources & evidence

ORD record
ord-a21901044c9f433fadfbdc5559bdda52
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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