Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Bromoacetonitrile | HCID 11534 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 117987652 | HCID 117987652 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 117987873 | HCID 117987873 | — |
Reaction Steps
To a solution of 1-cyclopentyl-4-methoxy-3-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile (152.2 mg) obtained in Step A of Example 98 in THF (2 mL) was added sodium hydride (dispersion in mineral oil, 39.6 mg) at 0° C., and the mixture was stirred for 1 hr. To the reaction mixture was added 2-bromoacetonitrile (38 μL) at 0° C., and the mixture was allowed to be warmed to room temperature, and stirred overnight. The reaction mixture was added to water, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (13.7 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09371320B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-45f2a28f4dcb4c988ca69597989c3299 |
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| Source note | uspto-grants-2016_06 |
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