Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 2-Amino-4-(methoxycarbonyl)benzeneboronic acid hydrochloride | HCID 16427083 | — |
| Reactant | Methyl 2-bromothiophene-3-carboxylate | HCID 53302196 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 50941659 | HCID 50941659 | 50% |
Reaction Steps
In a microwave vessel, methyl 2-bromo-3-thiophene carboxylate (1.0 eq, 260 mg, 1.18 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid hydrochloride (1.1 eq, 300 mg, 1.30 mmol), sodium acetate (3.0 eq, 292 mg, 3.56 mmol) and PdCl2(dppf) (0.05 eq, 31 mg, 0.059 mmol) were mixed together in anhydrous DMF (2 ml). The mixture was heated in a microwave oven at 120° C. for 10 nm. Water was added and the solid filtered and dried. The material was suspended in CH2Cl2, filtered and dried to afford methyl 4-oxo-4,5-dihydrothieno[3,2-c]quinoline-7-carboxylate as a yellow solid (152 mg, 50% yield). LCMS (ES): 95% pure, m/z 260 [M+1]+; 1H NMR (CDCl3, 400 MHz) δ 3.99 (s, 3H), 7.54 (d, J=5.2, 1H), 7.79 (d, J=4.8, 1H), 7.86 (d, J=8.4, 1H), 7.91 (dd, J=8.4, J=1.6, 1H), 8.03 (d, J=1.2, 1H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08168651B2 |
|---|
| Source dataset | uspto-grants-2012_05 |
|---|
| ORD ID | ord-14c5b14edb634e84aa990e16afbcd36d |
|---|
| Source note | uspto-grants-2012_05 |
|---|
