Water → HCID 22112790, compound

HRID 564725Notes

Reaction equation

[H-].[Na+].C(S)C.[CH2:6]([C:8]1[O:19][C:11]2=[C:12]([O:17]C)[N:13]=[CH:14][C:15]([Br:16])=[C:10]2[CH:9]=1)[CH3:7].O>CN(C)C=O>[Br:16][C:15]1[C:10]2[CH:9]=[C:8]([CH2:6][CH3:7])[O:19][C:11]=2[C:12](=[O:17])[NH:13][CH:14]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of sodium hydride (50 mg) (60% suspension in mineral oil) in dry N,N-dimethylformamide (3 ml) under an atmosphere of dry nitrogen at room temperature was added dropwise a solution of ethanethiol (0.09 ml) in N,N-dimethylformamide (3 ml). After stirring for 10 mins a solution of 2-ethyl-4-bromo-7-methoxyfuro[2,3-c]pyridine (200 mg) in N,N-dimethylformamide (5 ml) was added dropwise and the reaction mixture heated at 150° C. for 60 mins. Water (5 ml) was added and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (100 ml), washed with ammonium chloride solution (25 ml), water (25 ml) and brine (25 ml), dried over magnesium sulphate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with ethyl actate afforded the title compound as a white solid (169 mg).

Workup

additionwas added dropwise
customthe solvent removed in vacuo
dissolutionThe residue was dissolved in ethyl acetate (100 ml)
washwashed with ammonium chloride solution (25 ml), water (25 ml) and brine (25 ml)
dry with materialdried over magnesium sulphate
filtrationfiltered
customthe solvent removed in vacuo
customPurification by column chromatography on silica eluting with ethyl actate

Sources & evidence

ORD record: ord-890684084c57448d96a089f311cf033f
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169090A

Reaction notes

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