4-Methylmorpholine → Methyl 4-(4-fluoropicolinamido)thiophene-2-carboxylate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[NH2:42][C:43]1[CH:44]=[C:45]([C:48]([O:50][CH3:51])=[O:49])[S:46][CH:47]=1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:42][C:43]2[CH:44]=[C:45]([C:48]([O:50][CH3:51])=[O:49])[S:46][CH:47]=2)=[O:10])[CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 4-fluoropicolinic acid (1.0 g, 6.4 mmol), HATU (2.9 g, 7.6 mmol), and N-methylmorpholine (0.84 mL, 7.6 mmol) in N,N-dimethylformamide (12 mL) was stirred at 0° C. for 30 minutes. Methyl 4-aminothiophene-2-carboxylate (990 mg, 7.0 mmol) was added, the reaction was stirred for 30 minutes at 0° C., then warmed to room temperature, and stirred for an additional 2 hours. The solvent was removed under reduced pressure, the residue was suspended in acetonitrile/H2O (1:1) and the solids were isolated by filtration, washed with water, acetonitrile, then dried to afford methyl 4-(4-fluoropicolinamido)thiophene-2-carboxylate as a white powder (1.0 g, 56% yield). M+1=281.1.
Workup
- temperaturewarmed to room temperature
- stirringstirred for an additional 2 hours
- customThe solvent was removed under reduced pressure
- customthe solids were isolated by filtration
- washwashed with water, acetonitrile
- customdried
Sources & evidence
- ORD record
- ord-6680b7f8ed3545488ba8450c339e8c12
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440665B2
Reaction notes
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