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2-Amino-5-(trifluoromethyl)pyridine → Phenyl[6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methanone hydrobromide

HRID 600616
Notes
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Reaction equation

HRID 600616 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[Br:12][CH2:13][C:14](=O)[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16]>CN(C=O)C>[BrH:12].[C:17]1([C:15]([C:14]2[N:1]=[C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N:3]3[CH:13]=2)=[O:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7358622-Amino-5-(trifluoromethyl)pyridineHCID 125689113-Bromo-1-phenylpropane-1,2-dione

Product 1

HCID 67273541Phenyl[6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methanone hydrobromideYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
4 °C

Procedure

To a solution of 0.324 g of 2-amino-5-trifluoromethylpyridine in 4 mL of DMF cooled to 4° C. is added dropwise a solution of 0.65 g of 3-bromo-1-phenylpropane-1,2-dione in 11 mL of DMF. The reaction mixture is stirred for 16 hours at 4° C. The precipitate is filtered off and washed with diethyl ether, and then dried. 0.32 g of phenyl[6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]methanone hydrobromide (1:1) is obtained in the form of a white solid.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-1fbcf3a0569b4952806c2985a0036409
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902219B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes