Water → methyl 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=1[C:18]#[N:19].CO[CH:22]1[CH2:26][CH2:25][CH:24](OC)O1.O>C(O)(=O)C>[C:18]([C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][N:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][C:2]=1[N:1]1[CH:22]=[CH:26][CH:25]=[CH:24]1)#[N:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
131 mg of methyl 2-(4-amino-3-cyanophenyl)isonicotinate and 67 μl of 2,5-dimethoxytetrahydrofuran were dissolved in 1.3 ml of acetic acid solution, followed by heating and stirring at 100° C. for 4 hours. The solution was poured into water, followed by extraction with ethyl acetate. The solvent of the organic layer was evaporated under reduced pressure, and the residue was purified by column chromatography (hexane:ethyl acetate=10:1 to 1:1) to obtain 100 mg of methyl 2-[3-cyano-4-(1H-pyrrol-1-yl)phenyl]isonicotinate.
Workup
- temperatureby heating
- extractionfollowed by extraction with ethyl acetate
- customThe solvent of the organic layer was evaporated under reduced pressure
- customthe residue was purified by column chromatography (hexane:ethyl acetate=10:1 to 1:1)
Sources & evidence
- ORD record
- ord-e6d3cef1610646a3874d7df7e08b8260
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07816558B2
Reaction notes
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