Tetrahydrofuran → 6-Fluoro-1-methyl-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 707410Notes

Reaction equation

HRID 707410 reaction equation
[F:1][C:2]1[CH:3]=C(NC)C(N)=[N:6][CH:7]=1.[C:11]([N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1)(N1C=CN=C1)=O.C1C[O:26]CC1>C(=O)(O)[O-].[Na+]>[F:1][C:2]1[CH:3]=[C:22]2[N:18]([CH3:11])[C:19](=[O:26])[NH:20][C:21]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86694278HCID 86694278, compound

Product 1

HCID 866942796-Fluoro-1-methyl-1H-imidazo[4,5-B]pyridin-2(3H)-oneYield 64.3%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

5-Fluoro-N3-methylpyridine-2,3-diamine (0.399 g, 2.83 mmol) and 1,1′-carbonyldiimidazole (0.917 g, 5.65 mmol) were mixed in THF (12 mL). The reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted three times with EtOAc. The combined organic layers were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude brown solid was triturated with DCM and filtered to yield the title compound (0.304 g, 1.819 mmol, 64.3% yield) as a gray solid. M+1: 168.1.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting crude brown solid was triturated with DCM
  7. filtrationfiltered

Sources & evidence

ORD record
ord-6da7059ad3054bf1be203704a706c4c0
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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