Water → HCID 178471916, compound

HRID 226927Notes

Reaction equation

Cl.[CH3:2][C:3]1[C:4]([CH3:12])=[N:5][CH:6]=[C:7]([CH:11]=1)[C:8](Cl)=[O:9].[H-].[Na+].[CH2:15]([O:17][C:18](=[O:28])[CH:19]=[CH:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:16].O>O1CCCC1>[CH2:15]([O:17][C:18](=[O:28])[C:19]([C:8]([C:7]1[CH:6]=[N:5][C:4]([CH3:12])=[C:3]([CH3:2])[CH:11]=1)=[O:9])=[CH:20][NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:16]

Participants

Conditions

Temperature: -10 °C

Procedure

3.31 g (16.0 mmol) of 5,6-dimethyl-nicotinoyl chloride hydrochloride 6a (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) was dissolved in 35 mL of dry tetrahydrofuran and cooled down to −10° C. under nitrogen atmosphere. To the resultant solution was added 1.60 g (40.0 mmol) of 60% sodium hydride and the mixture was stirred for 15 minutes, followed by the addition of 3.06 g (16.0 mmol) of 3-phenylamino-acrylic acid ethyl ester 5a. The mixture was stirred at −10° C. for 2 hours, followed by the addition of 100 mL of water to the reaction mixture. The product was extracted twice with 100 mL dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated in vacuo. Purification of the crude product using flash chromatography (10-75% ethyl acetate in hexane) yielded 400 mg of 2-(5,6-dimethyl-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester 2d as a yellow solid.

Workup

stirringThe mixture was stirred at −10° C. for 2 hours
extractionThe product was extracted twice with 100 mL dichloromethane
dry with materialThe combined organic extracts were dried with MgSO4
concentrationconcentrated in vacuo
customPurification of the crude product

Sources & evidence

ORD record: ord-4236e405c3b24c7e8130a89210ca8e7e
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557213B2

Reaction notes

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