Water → HCID 86717935, compound

HRID 1844201Notes

Reaction equation

HRID 1844201 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Br[CH2:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[CH:23]=[CH:22][C:21]=1[F:28].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:12][C:10]1[N:11]=[C:3]2[C:2]([O:1][CH2:19][C:20]3[C:21]([F:28])=[CH:22][CH:23]=[C:24]([F:27])[C:25]=3[F:26])=[CH:7][C:6]([CH3:8])=[CH:5][N:4]2[C:9]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5190612,3,6-Trifluorobenzyl bromideHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 86717935HCID 86717935, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 g (42.69 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A, 10.9 g (46.96 mmol) of 2-(bromomethyl)-1,3,4-trifluorobenzene and 30.6 g (93.91 mmol) of caesium carbonate were initially charged in 611 ml of DMF, and the mixture was heated in an oil bath, preheated to 60° C., for 30 min. The reaction mixture was poured into about 5 l of water and stirred for 30 min, and the solid formed was filtered off with suction, washed with water and dried under high vacuum. This gave 14.1 g of the target compound (86% of theory).

Workup

  1. temperaturethe mixture was heated in an oil bath
  2. customthe solid formed
  3. filtrationwas filtered off with suction
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-854508bab60f487b97b2a533b2551346
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

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