Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | HCID 70979095 | HCID 70979095 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 70979181 | HCID 70979181 | 50.8% |
Reaction Steps
A mixture of 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzonitrile (150 mg, 0.37 mmol), triphenylphosphine (194 mg, 0.74 mmol) and diacetoxypalladium (8.3 mg, 0.037 mmol) in mixed solution of ethanol (6 mL) and water (2 mL) was heated at 60° C. for 30 minutes under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL*3). The organic phase was separated, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to give a crude product, which was purified by column chromatography (silica gel, dichloromethane/methanol=15:1) to afford 4-(8-(6-aminopyridin-3-yl)-1,4-dimethyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-6(5H)-yl)benzamide as a white solid (80 mg, 50.8%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09422292B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1a0df89ec394402a982e32445d920266 |
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| Source note | uspto-grants-2016_08 |
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