HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1908715Generated: October 26, 2026
Potassium Carbonate → 2-Propenyl-6-methylisonicotinic acid ethyl ester
https://huagongshe.com/reaction/1908715
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | ((1E)-prop-1-en-1-yl)boronic acid | HCID 6157276 | — |
| Reactant | Ethyl 2-Chloro-6-methylisonicotinate | HCID 22625009 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 2-Propenyl-6-methylisonicotinic acid ethyl ester | HCID 67027102 | 109.6% |
Reaction Steps
To a solution of 2-chloro-6-methylisonicotinic acid ethyl ester (2.0 g, 10.0 mmol), and trans-propenyl boronic acid (1.30 g, 15.13 mmol) in DME (20 mL), a solution of 2 M aq. K2CO3 (3 mL) followed by Pd(PPh3)4 (150 mg, 0.205 mmol) and triphenylphosphine (265 mg, 0.99 mmol) is added. The mixture is stirred at 100° C. for 15 h before it is cooled to rt, diluted with diethyl ether and washed with sat. aq. Na2CO3 (2×30 mL). The org. extract is dried over Na2SO4, filtered and evaporated. The crude product is purified by CC on silica gel eluting with heptane:EA 4:1 to give 2-propenyl-6-methylisonicotinic acid ethyl ester (2.25 g) as a colourless oil; LC-MS: tR=0.65 min, [M+1]+=206.33.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08598208B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-4f5607698ded469e8f1f36ee0c1aa01b |
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| Source note | uspto-grants-2013_12 |
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