Methyl 3-aminopyrazinecarboxylate → Methyl 2-(4-fluorophenyl)imidazo[1,2-a]pyrazine-8-carboxylate
Reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[NH2:12][C:13]1[C:14]([C:19]([O:21][CH3:22])=[O:20])=[N:15][CH:16]=[CH:17][N:18]=1>C(#N)C>[CH3:22][O:21][C:19]([C:14]1[C:13]2[N:18]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=3)[N:12]=2)[CH:17]=[CH:16][N:15]=1)=[O:20]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 2-bromo-1-(4-fluorophenyl)ethanone (30.0 g, 138 mmol) and methyl 3-aminopyrazine-2-carboxylate (21.2 g, 138 mmol) in ACN (300 mL) was heated at about 80° C. The mixture was removed from heat after about 72 h and concentrated under reduced pressure. The crude material was partitioned between saturated aqueous NaHCO3 (450 mL) and DCM (350 mL). The layers were separated and the aqueous layer was washed with additional DCM (2×250 mL). The combined organic layers were washed with water (3×350 mL) and brine (20 ml) then dried over MgSO4, filtered, and concentrated under reduced pressure to give the crude title compound (38.7 g, 45.5%) that was carried on without further purification. LC/MS (Table 1, Method h) Rt=2.26 min; MS m/z: 272.2 (M+H)+.
Workup
- customThe mixture was removed
- temperaturefrom heat after about 72 h
- concentrationconcentrated under reduced pressure
- customThe crude material was partitioned between saturated aqueous NaHCO3 (450 mL) and DCM (350 mL)
- customThe layers were separated
- washthe aqueous layer was washed with additional DCM (2×250 mL)
- washThe combined organic layers were washed with water (3×350 mL) and brine (20 ml)
- dry with materialthen dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-f0b491488e1b453c8e0eb68115a6128b
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709468B2
Reaction notes
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