Dimethylformamide → Methyl 5-(3-aminophenyl)thiophene-2-carboxylate
Reaction equation
[S:1](O)(O)(=O)=O.[NH2:6][C:7]1[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][CH:12]=1.N[C:17]1[CH:18]=[C:19](B(O)O)C=C[CH:22]=1.[C:26](=[O:29])([O-])[O-].[Na+].[Na+].CN([CH:35]=[O:36])C>C(OCC)(=O)C>[CH3:26][O:29][C:35]([C:22]1[S:1][C:19]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([NH2:6])[CH:8]=2)=[CH:18][CH:17]=1)=[O:36]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of compound N-1 (1.6 g, 7.20 mmol), 3-aminophenylboronic acid hemisulfate (1.60 g, 8.60 mmol), Palladium tetrakis triphenylphosphine (0.25 g, 0.216 mmol), sodium carbonate (40 mL, 2M, 82 mmol) in DMF (100 mL) was stirred for 2 hrs at 80° C. overnight. The solvent was removed and the crude reaction product was taken up in ethyl acetate (40 mL). The solution was washed with 5% solution of hydrochloric acid (30 mL), then with saturated sodium chloride solution (30 mL), dried over sodium sulfate and evaporated. Purification of the residue on silica gel (1:1 hexanes-EtOAc) gave 0.790 g of compound N-2 (48% yield).
Workup
- customThe solvent was removed
- customthe crude reaction product
- washThe solution was washed with 5% solution of hydrochloric acid (30 mL)
- dry with materialwith saturated sodium chloride solution (30 mL), dried over sodium sulfate
- customevaporated
- customPurification of the residue on silica gel (1:1 hexanes-EtOAc)
Sources & evidence
- ORD record
- ord-ebde23dbf32c436b939272b7cfa9fdf2
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06274620B1
Reaction notes
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