Sodium hydride → 5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridine-3-carbaldehyde

HRID 11681Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:22]=[CH:21][C:7]([CH2:8][N:9]2[C@@H:14]([CH3:15])[CH2:13][N:12]([C:16](=[O:19])[CH2:17][OH:18])[C@H:11]([CH3:20])[CH2:10]2)=[CH:6][CH:5]=1.Cl[C:24]1[C:29]([CH:30]=[O:31])=[CH:28][C:27]([Cl:32])=[CH:26][N:25]=1>C1(C)C=CC=CC=1>[Cl:32][C:27]1[CH:28]=[C:29]([CH:30]=[O:31])[C:24]([O:18][CH2:17][C:16]([N:12]2[CH2:13][C@H:14]([CH3:15])[N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([F:3])=[CH:22][CH:21]=3)[CH2:10][C@H:11]2[CH3:20])=[O:19])=[N:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. suspension of sodium hydride (60% dispersion in mineral oil, 0.031 g, 0.78 mmol) in toluene (3 mL) was added 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone (0.20 g, 0.71 mmol) in toluene (2 mL). The reaction mixture was stirred at 0° C. for 30 minutes, and then treated with 2,5-dichloro-pyridine-3-carbaldehyde (0.14 g, 0.78 mmol). The resulting mixture was refluxed for 4 hours, cooled to ambient temperature and washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography provided the title compound (0.20 g).

Workup

temperatureThe resulting mixture was refluxed for 4 hours
temperaturecooled to ambient temperature
washwashed with saturated aqueous sodium hydrogen carbonate and brine
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-8d2580975c9440d99c5df9cc611230c9
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Reaction notes

Loading…