Water → HCID 86717874, compound

HRID 2275762Notes

Reaction equation

HRID 2275762 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 9A; 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, the mixture was stirred for 30 min and 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-e46e8a59471b4193b5c9097fb0cfba81
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

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