Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | HCID 86621472 | HCID 86621472 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 59305835 | HCID 59305835 | 90.1% |
Reaction Steps
The Suzuki procedure described for 28 was followed using triflate 25 (150 mg, 0.32 mmol), PdCl2(Ph3P)2 (23 mg, 0.032 mmol), 2 N aqueous Na2CO3 (320 uL, 3.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (334 mg, 1.6 mmol), and DME (2 mL). The mixture was heated at 120° C. for 5 min in the microwave. Aqueous work-up followed by purification gave 116 mg (90%) of the title product 31 as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.06 (s, 1H), 7.79 (s, 1H), 7.46 (d, J=8.0 Hz, 2H), 7.2-7.16 (m, 2H), 7.11 (d, J=8.0 Hz, 2H), 3.83 (s, 3H), 1.93 (s, 2H), 1.88 (s, 2H), 1.26 (s, 2H), 0.89 (s, 6H), 0.84 (s, 6H). LCMS (APCI): m/z 403 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07723393B2 |
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| Source dataset | uspto-grants-2010_05 |
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| ORD ID | ord-eaecb5524eb045e69e50b2e51f3375db |
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| Source note | uspto-grants-2010_05 |
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