Potassium Carbonate → Ethyl 6-bromo-1-(1,3-dimethoxypropan-2-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:17](F)=[CH:18][N:19]=1)[C:5]([C:7](=[CH:13]N(C)C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[CH3:21][O:22][CH2:23][CH:24]([NH2:28])[CH2:25][O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][N:19]=1)[N:28]([CH:24]([CH2:25][O:26][CH3:27])[CH2:23][O:22][CH3:21])[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 65, 1 g, 2.9 mmol, 1 equiv.) in THF (7 mL) was added 1,3-dimethoxypropan-2-amine (451 mL, 2.9 mmol, 1 equiv.). This reaction mixture was stirred at 60° C. for 1 h. The reaction mixture was concentrated under reduced pressure and re-suspended in DMF (7 mL). Potassium carbonate (1.2 g, 8.69 mmol, 3 equiv.) was added, and the reaction mixture was stirred at 70° C. for 3 h. The reaction mixture was cooled to room temperature and quenched with water. 1 N HCl was added until pH 4-5 was reached. The precipitate was washed with water and hexanes and dried to provide ethyl 6-bromo-1-(1,3-dimethoxypropan-2-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate as a solid (963 mg, 83%).
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- stirringthe reaction mixture was stirred at 70° C. for 3 h
- temperatureThe reaction mixture was cooled to room temperature
- customquenched with water
- addition1 N HCl was added until pH 4-5
- washThe precipitate was washed with water and hexanes
- customdried
Sources & evidence
- ORD record
- ord-ef3e54a764ed4b948fb48d7f9749e2bc
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569484B2
Reaction notes
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