4-Methylmorpholine → Methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[NH2:11][C:12]1[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[S:15][CH:16]=1.C[NH3+].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:11][C:12]2[CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[S:15][CH:16]=2)=[O:10])[CH:3]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-bromo-pyridine-2-carboxylic acid (1.98 g, 9.80 mmol), methyl 4-aminothiophene-2-carboxylate (1.40 g, 8.91 mmol), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyl uronium hexafluorophosphate methanaminium (HATU) (4.07 g, 10.7 mmol), and N-methylmorpholine (1.18 mL, 10.7 mmol) in N,N-dimethylformamide (18 mL) was stirred at room temperature for 6 hours. The solvent was removed under reduced pressure, the residue suspended in acetonitrile, and the solids were isolated by filtration. The solids were washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL), and dried under reduced pressure to afford methyl 4-(4-bromopicolinamido)thiophene-2-carboxylate, a compound of formula (19) as a white powder (2.70 g, 90% yield). M+1=341.1.
Workup
- customThe solvent was removed under reduced pressure
- customthe solids were isolated by filtration
- washThe solids were washed with water (80 mL), acetonitrile (80 mL) and diethyl ether (80 mL)
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-8f3bc4612d2e42dfa22640980557ab35
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08440665B2
Reaction notes
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