Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Reactant | HCID 66864796 | HCID 66864796 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66864394 | HCID 66864394 | — |
Reaction Steps
To a suspension of (2R)-6-amino-2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridine]-5-carbonitrile (200 mg, 0.72 mmol) in 25% HBr at 0° C. was added a solution of sodium nitrite (61.4 mg, 0.89 mmol) in H2O (0.3 mL) dropwise. The cooled mixture was then added to a cooled solution of copper(I)bromide (107 mg, 0.746 mmol) in 48% HBr (0.557 mL, 4.92 mmol). The reaction mixture was stirred at 0° C. for 1 h then warmed to ambient temperature. H2O (5 mL) was added and the mixture was made basic by addition of concentrated NH4OH. The resulting precipitate was collected by filtration and washed with H2O to provide the title compound in sufficient purity for the next step. MS: m/z=341 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08765759B2 |
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| Source dataset | uspto-grants-2014_07 |
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| ORD ID | ord-99266c55f18641d293f06daf83fa1284 |
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| Source note | uspto-grants-2014_07 |
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