Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 66604304 | HCID 66604304 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 66604909 | HCID 66604909 | 39.4% |
Reaction Steps
3-Bromo-4-fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (25 mg, 0.059 mmol), phenylboronic acid (10.88 mg, 0.089 mmol), Pd(Ph3P)4 (6.87 mg, 5.95 μmol) and Na2CO3(2M) (0.074 mL, 0.149 mmol) were mixed with toluene (2 mL) and MeOH (1 mL) in a sealed microwave tube. The mixture was stirred at 105° C. for 3 hrs. The mixture was filtered through a ACRODISC® PTFE membrane (0.45 um) and purified using preparative HPLC to give 9.7 mg of 4-fluoro-6-(morpholine-4-carbonyl)-3-phenyl-9H-carbazole-1-carboxamide. MS (ESI) m/z 418.06 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.9 (bs, 1H), 8.32 (bs, 1H), 8.19 (d, 1H, J=7.1), 8.15 (s, 1H), 7.84 (d, 1H, J=8.6), 7.72 (d, 2H, J=7.3), 7.62-7.53(m, 4H), 7.43 (t, 1H, J=7.3), 3.7-3.5 (bm, 8H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815840B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-757ab63009254bf98145a520b6abfcd1 |
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| Source note | uspto-grants-2014_08 |
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