Dimethylformamide → HCID 42629828, compound

HRID 254315Notes

Reaction equation

HRID 254315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[C:13]3[C:18]([N:19]=[C:20]([CH3:21])[C:11]2=[C:10]([CH3:23])[N:9]=1)=[CH:17][C:16]([OH:22])=[CH:15][CH:14]=3.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[F:35][C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:37]=1[CH2:38]Br>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[C:13]3[C:18]([N:19]=[C:20]([CH3:21])[C:11]2=[C:10]([CH3:23])[N:9]=1)=[CH:17][C:16]([O:22][CH2:38][C:37]1[C:36]([F:35])=[CH:43][CH:42]=[CH:41][C:40]=1[F:44])=[CH:15][CH:14]=3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 42629710HCID 42629710, compound

Product 1

HCID 42629828HCID 42629828, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
130 °C

Procedure

1 g 1-(2-Chloro-phenyl)-3,4-dimethyl-7-hydroxy-imidazo(1,5-a)quinoxaline, 2.24 g Caesium carbonate, 50 mL N,N-dimethylformamide, and 6 mL water were stirred for 10 min followed by addition of 0.83 g 2,6-difluorobenzylbromide. After 3 h stirring at 130° C. the reaction mixture was given into 150 mL water, filtered off, washed with water, dried under reduced pressure, and purified with silica gel, dichloromethane/methanol=95/5.

Workup

  1. filtrationfiltered off
  2. washwashed with water
  3. customdried under reduced pressure
  4. custompurified with silica gel, dichloromethane/methanol=95/5

Sources & evidence

ORD record
ord-720b6c95d79744c5b9668e0edb6b7010
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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