Dimethylformamide → 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 923790Notes

Reaction equation

HRID 923790 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([C:10]([F:13])([F:12])[F:11])=[CH:5][N:4]=1.[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.S([O-])(O)=O.[Na+].CN(C=O)C>O>[F:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]1[N:2]([CH3:1])[C:3]2=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]2[N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 67970o-FluorobenzaldehydeHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 23665763Sodium Bisulfite

Product 1

HCID 679818402-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 30.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
153 °C

Procedure

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (1.91 g), 2-fluorobenzaldehyde (1.86 g), sodium hydrogen sulfite (1.56 g), and DMF (10 ml) was stirred with heating under reflux at 153° C. for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.89 g of 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound (1E)-F1).

Workup

  1. temperaturewith heating
  2. temperatureInto the reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-445f888e63a4426687602248aba1553b
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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