Hydrochloric Acid → 2-(3-Fluorophenylaminocarbonyl)-7-methoxybenzofuran

HRID 1057939Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[H-].[Na+].[H][H].[CH3:13][O:14][C:15]1[C:23]2[O:22][C:21]([C:24](Cl)=[O:25])=[CH:20][C:19]=2[CH:18]=[CH:17][CH:16]=1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH:5][C:24]([C:21]2[O:22][C:23]3[C:15]([O:14][CH3:13])=[CH:16][CH:17]=[CH:18][C:19]=3[CH:20]=2)=[O:25])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, 3-fluoroaniline (6.2 ml) was dissolved in dry THF (150 ml), and the solution was stirred at 0° C. Sodium hydride (3.4 g) was slowly added to the mixture followed by stirring at 0° C. for 20 minutes. After the generation of hydrogen ceased, 7-methoxybenzofuran-2-carbonyl chloride (9.0 g) was added to the mixture, followed by stirring at room temperature for 3 hours. The reaction was stopped with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with a 1N aqueous solution of hydrochloric acid and with a saturated saline, and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was triturated with diethyl ether to give Compound IIbf-a (7.82 g, 64.2%) as a white solid.

Workup

stirringby stirring at 0° C. for 20 minutes
stirringby stirring at room temperature for 3 hours
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with a 1N aqueous solution of hydrochloric acid and with a saturated saline
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was triturated with diethyl ether
customto give Compound IIbf-a (7.82 g, 64.2%) as a white solid

Sources & evidence

ORD record: ord-7abd73a2cea644aeb257f1b2f01ecc96
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06514996B2

Reaction notes

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