Water → HCID 86717874, compound

HRID 1624067Notes

Reaction equation

HRID 1624067 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:17])[C:5]2[N:6]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:26]=1[CH2:27]Br.O>CN(C=O)C>[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:26]=1[CH2:27][O:17][C:4]1[C:5]2[N:6]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 86717873HCID 86717873, compound

Product 1

HCID 86717874HCID 86717874, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

560 mg of ethyl 6-fluoro-8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate (Example 12A; 2.4 mmol, 1.0 equivalent), 1.7 g of caesium carbonate (5.17 mmol, 2.2 equivalents) and 535 mg of 2,6-difluorobenzyl bromide (2.6 mmol, 1.1 equivalents) were initially charged in 34 ml of dry DMF, and the mixture was heated at 50° C. for 15 min. Water was added and the mixture was stirred for 30 min. The solid was filtered off and washed with water. This gave 560 mg of the title compound (65% of theory).

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water

Sources & evidence

ORD record
ord-8636b34ad55d44f2a6ce6da6adb35ca3
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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