Sodium Bicarbonate → 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine

HRID 1477287Notes

Reaction equation

HRID 1477287 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[C:16]([CH:21]=O)=[N:17][CH:18]=[CH:19][CH:20]=1.S([O-])(O)=O.[Na+].C(=O)([O-])O.[Na+]>CN(C=O)C>[F:14][C:15]1[C:16]([C:21]2[N:2]([CH3:1])[C:3]3=[N:4][CH:5]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:8]3[N:9]=2)=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 2735930N2-Methyl-5-(trifluoromethyl)pyridine-2,3-diamineHCID 113440173-Fluoro-2-pyridinecarboxaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 712468362-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridineYield 36.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of N2-methyl-5-trifluoromethylpyridin-2,3-diamine (0.76 g), 3-fluoropyridin-2-carboaldehyde (0.50 g), sodium hydrogen sulfite (0.50 g) and DMF (3 ml) was stirred at 120° C. for 8 hours. To the cooled reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2-(3-fluoropyridin-2-yl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.43 g), which is hereinafter referred to as “intermediate compound (M6-2)”.

Workup

  1. customTo the cooled reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf3c175ec05243f3956b399bf7e765fd
Source dataset
uspto-grants-2016_08
Patent number
US09403771B2

Reaction notes

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