HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2279138Generated: October 30, 2026
Water → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester
https://huagongshe.com/reaction/2279138
Participants
| Role | Name | HCID | Charge |
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| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 4-(Methoxymethoxy)phenylboronic acid | HCID 2762528 | — |
| Reactant | 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester | HCID 86680319 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester | HCID 90013795 | 107.1% |
Reaction Steps
To a degassed mixture of 1.68 g 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester, 1.00 g 4-(methoxymethoxy)-phenylboronic acid and 0.70 g potassium carbonate in DME/water (v/v=2/1, 24 mL) at r.t. and under Ar-atmosphere 70 mg palladium(0) bis(tri-tert-butylphosphine) was added and the mixture was stirred at 85° C. for 1 h. To the mixture water and ethyl acetate were added, the phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. 2.08 g (100%) of the title compound were obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09133181B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-5604f7e767dd46a0910abfac81f3d725 |
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| Source note | uspto-grants-2015_09 |
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