Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2,6-Difluorobenzamide | HCID 87439 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 59513693 | HCID 59513693 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59513720 | HCID 59513720 | 66% |
Reaction Steps
To an oven-dried flask under N2 was added 4-[2-(3-bromophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-5-fluoro-N-(3-fluorophenyl)-2-pyrimidinamine (40 mg, 0.08 mmol), anhydrous degassed 1,4-dioxane (10 mL), Pd2(dba)3 (13.4 mg, 0.01 mmol), Xantphos (12.7 mg, 0.02 mmol), 2,6-difluorobenzamide (34.5 mg, 0.2 mmol), and Cs2CO3 (83 mg, 0.26 mmol). The reaction was heated in the microwave at 160° C. for 15 min, adsorbed to silica gel, and purified by LC (DCM to 5% MeOH/DCM) to afford the desired product (30 mg, 66%) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 6.63-6.67 (m, 1H), 7.10-7.25 (m, 4H), 7.29-7.34 (m, 2H), 7.39-7.47 (m, 1H), 7.53-7.59 (m, 1H), 7.68-7.70 (m, 2H), 8.04-8.10 (m, 2H), 8.60 (s, 1H), 9.57 (s, 1H), 9.97 (s, 1H), 10.87 (s, 1H); ESIMS (M+H)+=623.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07812022B2 |
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| Source dataset | uspto-grants-2010_10 |
|---|
| ORD ID | ord-fcea2cc23d20480abaa1801b0fc0d424 |
|---|
| Source note | uspto-grants-2010_10 |
|---|
