Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | HCID 66604304 | HCID 66604304 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 66604776 | HCID 66604776 | 46.2% |
Reaction Steps
3-Bromo-4-fluoro-6-(morpholine-4-carbonyl)-9H-carbazole-1-carboxamide (25 mg, 0.059 mmol), 4-methoxyphenylboronic acid (13.56 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 an ACRODISC® PTFE membrane (0.45 um) and purified using preparative HPLC to give 12.2 mg of titled product. MS (ESI) m/z 448.06 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.86 (bs, 1H), 8.31 (bs, 1H), 8.16 (d, 1H, J=9.1), 8.14 (s, 1H), 7.83 (d, 1H, J=8.6), 7.66 (d, 2H, J=8.2), 7.55(m, 2H), 7.11 (d, 2H, J=8.5), 3.84 (s, 3H), 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-2641bc9be3d347198934facf55bf42d4 |
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| Source note | uspto-grants-2014_08 |
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