3-Pyridinecarboxaldehyde → 4-(3,4-Dichloro-phenyl)-5-pyridin-4-yl-1-pyridin-3-ylmethyl-pyrazolidin-3-one

HRID 1064087Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[NH:12][NH:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:12]([CH2:27][C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)[NH:11][C:10]2=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-(3,4-Dichloro-phenyl)-5-pyridin-4-yl-pyrazolidin-3-one 0.30 g and 0.12 mL 3-pyridinecarboxaldehyde in chloroform 20 mL was added NaBH3(CN) 0.1 g at 0° C., the reaction was warmed 50° C. and stirred for 1 hour. The reaction was quenched with sat.NaHCO3 25 mL at 0° C. The reaction mixture was extracted with dichloromethane, 3×50 mL. The combined organic phase was washed with brine, dried over anhydrous Na2SO4. After purification by flash chromatography, the title compound was obtained as yellow solid 0.28 g. MS (ES+): 399 (M+H)+.

Workup

customThe reaction was quenched
customat 0° C
extractionThe reaction mixture was extracted with dichloromethane, 3×50 mL
washThe combined organic phase was washed with brine
dry with materialdried over anhydrous Na2SO4
customAfter purification by flash chromatography

Sources & evidence

ORD record: ord-da49188a53f040cca922fd7e6b010322
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06967254B2

Reaction notes

Loading…