Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 21543699 | HCID 21543699 | — |
| Reactant | 5-(2-Methyl-1-(trifluoromethoxy)propan-2-yl)pyridin-3-ylboronic acid | HCID 70981237 | — |
| Catalyst | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| Solvent | Water | HCID 962 | — |
| Product | Trifluoroacetic acid | HCID 6422 | — |
| Product | 7-{5-[2-Methyl-1-(trifluoromethoxy)-2-propanyl]-3-pyridinyl}-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoline | HCID 66576771 | — |
Reaction Steps
To a vial containing the title compound from Example 22 Step B (50 mg, 0.200 mmol), the title compound from Example 64 Step C (63.1 mg, 0.240 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (28.3 mg, 0.040 mmol) and potassium carbonate (83 mg, 0.600 mmol) were added tert-butanol (2.2 mL) and water (0.28 mL). The vial was capped tightly and heated to 80° C. overnight. The reaction was then cooled to room temperature and concentrated under reduced pressure. The resulting residue was diluted with acetonitrile and then purified by HPLC (C18 column, 10 to 100% acetonitrile/water, both 0.1% v/v trifluoroacetic acid) to provide the title compound: LCMS m/z 389.00 [M+H]+; NMR (500 MHz, CD3OD) δ 9.99 (s, 1H), 9.19 (s, 1H), 9.02 (s, 1H), 8.94 (s, 1H), 8.09-8.00 (m, 3H), 4.33 (s, 2H), 3.48-3.45 (m, 2H), 3.39-3.36 (m, 2H), 1.60 (s, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073929B2 |
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| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-f14590fb1c4a4e0899a717956ae759aa |
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| Source note | uspto-grants-2015_07 |
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