HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1776810Generated: November 4, 2026
Sodium Bicarbonate → HCID 136341363, compound
https://huagongshe.com/reaction/1776810
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 6-Chloro-2-iodo-3-hydroxypyridine | HCID 23433158 | — |
| Reactant | (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid | HCID 57562462 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 136341363 | HCID 136341363 | 59.1% |
Reaction Steps
To a degassed solution of (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (500 mg, 1.17 mmol), NaHCO3 (287 mg, 3.42 mmol) and 6-chloro-2-iodopyridin-3-ol (525 mg, 2.05 mmol) in 1,4-dioxane (10 mL) was added Pd(dppf)Cl2 (10 mg) under N2. The mixture was heated at 70° C. for 5 hours, concentrated in vacuo to remove 1,4-dioxane and extracted with EtOAc. After washed with brine and dried over Na2SO4, the solvent was removed by distillation. After concentrated, the crude product of tert-butyl 2-(6-chloro-3-hydroxypyridin-2-yl)-5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (260 mg, yield: 40%). MS (M+H)+: 376/378.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09265773B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-2e22e5d338cb4c138fb5a48f1dfb3e40 |
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| Source note | uspto-grants-2016_02 |
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