Dimethyl Sulfoxide → 4'-Methyl-N-((6-methylpyridin-3-yl)methyl)-5-(oxiran-2-yl)biphenyl-3-carboxamide

HRID 1845341Notes

Reaction equation

HRID 1845341 reaction equation
[H-].[Na+].[I-].[CH:4]([C:6]1[CH:7]=[C:8]([C:19]([NH:21][CH2:22][C:23]2[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=2)=[O:20])[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[CH:11]=1)=[O:5].[CH3:30]S(C)=O>>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([C:10]2[CH:11]=[C:6]([CH:4]3[CH2:30][O:5]3)[CH:7]=[C:8]([C:19]([NH:21][CH2:22][C:23]3[CH:24]=[N:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[O:20])[CH:9]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 679Dimethyl Sulfoxide3×HCID 24758Sodium hydrideHCID 30165Iodide IonHCID 581882015-Formyl-4'-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide

Product 1

HCID 581883944'-Methyl-N-((6-methylpyridin-3-yl)methyl)-5-(oxiran-2-yl)biphenyl-3-carboxamide

Conditions

Temperature
-10 °C

Procedure

A mixture of sodium hydride (60% in mineral oil, 0.85 g, 21.2 mmol) in dimethyl sulfoxide (75 mL) was cooled to −10° C. Trimethylsufoxonium iodide (4.66 g, 21.2 mmol) in DMSO (25 mL) was added dropwise over a 10 mM period. The mixture was warmed to room temperature and stirred for an additional hour. The mixture was cooled to 0° C. and 5-formyl-4′-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide (3.65 g, 10.6 mmol) in DMSO (25 mL) was added dropwise over a 10 minute period. The mixture was warmed to room temperature and stirred for 1 hour. The mixture was poured onto ice and extracted with ethyl acetate (3×150 mL). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The mixture was purified by column chromatography using methylene chloride:methanol gradient (2-10%) to afford the title compound as a yellow oil. LC-MS: 358.8 [M+1]+.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. temperatureThe mixture was cooled to 0° C.
  3. temperatureThe mixture was warmed to room temperature
  4. stirringstirred for 1 hour
  5. additionThe mixture was poured onto ice
  6. extractionextracted with ethyl acetate (3×150 mL)
  7. dry with materialThe combined extracts were dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-ba7cba8e3c614b73a9712e60d5520177
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…