Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 5-bromo-1H-indazole | HCID 761929 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | 1H-Indazole-5-carbonitrile | HCID 11126384 | 24% |
Reaction Steps
To a suspension of 5-bromo-indazole (2.0 g, 10.2 mmol), Zn(CN)2 (1.4 g, 12.2 mmol), and Xantphos (0.9 g, 1.5 mmol), in DMF (10 mL) and water (0.1 mL) was added Pd2(dba)3 (417 mg, 0.51 mmol) under N2 at rt. The suspension was heated at 150° C. for 1.5 h in the microwave. The solution was filtered and concentrated, and the residue was purified by silica gel chromatography (10-20% MeOH/DCM) to give 350 mg (24%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.62 (2H, s), 8.20 (2H, d, J=8.0 Hz), 10.56 (1H, br s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08969343B2 |
|---|
| Source dataset | uspto-grants-2015_03 |
|---|
| ORD ID | ord-477c461a16cd468e84fb914ab2728c60 |
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| Source note | uspto-grants-2015_03 |
|---|
