Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 59859943 | HCID 59859943 | — |
| Reactant | HCID 86683444 | HCID 86683444 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 56597463 | HCID 56597463 | — |
Reaction Steps
To the stirred solution (2-(cyanoimino)-1-(4-(2-cyanopropan-2-yl)phenyl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)boronic acid (0.390 mmol) in dry DMF (5 ml) was added N-(5-bromo-2-methoxypyridin-3-yl)benzenesulfonamide (0.39 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.039 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated at 111° C. for 8 minutes in microwave. Solvent was removed and the crude material was extracted with EtOAc, washed with brine several times and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, CHCl3/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.23 (s, 1H), 8.20 (d, J=8.7 Hz, 1H), 7.88 (s, 4H), 7.84 (m, 1H), 7.70 (m, 4H), 7.56 (m, 3H), 6.83 (s, 1H), 3.92 (s, 3H), 3.58 (s, 3H), 1.81 (s, 6H); MS (m/z): 629 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09062046B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-a71377fb55b44619a289c61bb2a88f44 |
|---|
| Source note | uspto-grants-2015_06 |
|---|