[5-(Trifluoromethyl)-2-furyl]methanol → HCID 89690250, compound

HRID 2203008Notes

Reaction equation

HRID 2203008 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH3:20])=[C:15]([CH:17]4[CH2:19][CH2:18]4)[N:16]=3)[CH:13]=2)[C:4](=[O:21])[CH:3]=1.[F:22][C:23]([F:32])([F:31])[C:24]1[O:28][C:27]([CH2:29][OH:30])=[CH:26][CH:25]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH:17]1([C:15]2[N:16]=[C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH:6]=[CH:7][C:2]([O:30][CH2:29][C:27]5[O:28][C:24]([C:23]([F:32])([F:22])[F:31])=[CH:25][CH:26]=5)=[CH:3][C:4]4=[O:21])=[CH:13][N:12]3[C:14]=2[CH3:20])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 7537667[5-(Trifluoromethyl)-2-furyl]methanolHCID 23665647Potassium tert-butoxideHCID 1213862044-Bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone

Product 1

HCID 89690250HCID 89690250, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 4-bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)pyridin-2(1H)-one (120 mg) and (5-(trifluoromethyl)furan-2-yl)methanol (87 mg) in toluene (2 ml) was added potassium tert-butoxide (117 mg) at room temperature, and the mixture was stirred at 100° C. for 1 h. The mixture was quenched with water, and the precipitate was collected by filtration and washed with IPE to give the title compound (75 mg) as a yellow solid.

Workup

  1. customThe mixture was quenched with water
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with IPE

Sources & evidence

ORD record
ord-fac9d60f4d2146c9812c0a9bfb57567f
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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