Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 73013588 | HCID 73013588 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67155969 | HCID 67155969 | 65% |
Reaction Steps
Sodium tetrahydroborate (0.069 g, 1.81 mmol) was added to a solution of 5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (200 mg, 0.60 mmol) in THF (3.8 mL) and methanol (0.4 mL) at −40° C. The mixture was stirred at −40° C. for 30 minutes. The reaction mixture was then treated with water and ethyl acetate, and the layers were separated. The aqueous layer was extracted once with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford (5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol (0.13 g, 65%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08338452B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-ee7d495fbdc24546a23e31137c79c4a0 |
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| Source note | uspto-grants-2012_12 |
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