Trifluoroacetic acid → 6-[(3-Chloro-pyridin-4-ylmethyl)-amino]-nicotinic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[N:6][CH:5]=1.[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[CH:19]=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(#N)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:19][C:18]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[Cl:12])=[N:6][CH:5]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 6-amino-nicotinic acid methyl ester (553, 2.15 g, 0.014 mol) in acetonitrile (60.0 mL) were added 3-chloro-pyridine-4-carbaldehyde (554, 2.00 g, 0.014 mol), triethylsilane (11.00 mL, 0.069 mol) and trifluoroacetic acid (5.00 mL, 0.065 mol). The reaction was stirred at 80° C. overnight. The reaction was concentrated, poured into aqueous potassium carbonate, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound (555, 1.5 g, 38.2%). MS (ESI) [M+H+]+=278.9.
Workup
- concentrationThe reaction was concentrated
- additionpoured into aqueous potassium carbonate
- extractionextracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated
- custompurified by silica gel column chromatography
- washeluting with 20% to 100% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-443dadac25084041a321c62bd101d7e3
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08404700B2
Reaction notes
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