Sodium ethoxide → 7-(4-Amino-3-fluorophenoxy)-1-N-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one

HRID 2272679Notes

Reaction equation

[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[C:8]=2[N:14]([CH3:20])[C:15](=O)[O:16]CC)=[CH:4][C:3]=1[F:23].CC[O-].[Na+].[Na]>CCO>[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][C:15](=[O:16])[N:14]([CH3:20])[C:8]=23)=[CH:4][C:3]=1[F:23]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 4-(4-amino-3-fluorophenoxy)-2-aminopyridin-3-yl-methyl-carbamate (7a) (320 mg, 1.0 mmol) was suspended in a solution of EtONa in EtOH (4 mL), obtained from dissolving sodium (480 mg, 21 mmol) in ethanol (9 mL). The suspension was heated under microwave irradiation for 1 hour (100° C., 100 W). The mixture was cooled at room temperature and the solvent was evaporated. The residue was dissolved in water and was acidified with AcOH to pH 4. The precipitate formed was recovered by filtration, to afford the title compound.

Workup

customobtained
temperatureThe mixture was cooled at room temperature
customthe solvent was evaporated
dissolutionThe residue was dissolved in water
customThe precipitate formed
filtrationwas recovered by filtration

Sources & evidence

ORD record: ord-30bded027ce64b7a9a14582a5b708fc9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120789B2

Reaction notes

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