Dimethyl Sulfoxide → HCID 59633179, compound

HRID 2369058Notes

Reaction equation

HRID 2369058 reaction equation
Br[CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[N:4]=1.[C-:30]#[N:31].[Na+].CS(C)=O>O>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[N:5]1[C:6]([C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:14]=3)=[CH:11][CH:12]=2)=[CH:7][C:3]([CH2:2][C:30]#[N:31])=[N:4]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 59632228HCID 59632228, compound

Product 1

HCID 59633179HCID 59633179, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the 3-bromomethyl-1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-thiophen-2-yl]-1H-pyrazole (720 mg, 1.42 mmol), NaCN (250 mg, 5.1 mmol), and DMSO (10 mL) was stirred in a sealed vial at 100° C. for 5 h, diluted with water, and extracted with EtOAc. The combined extracts were washed with water, brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-80% EtOAc/hexanes) to give the title compound as a white solid (350 mg, 54%). 1HNMR (CDCl3): δ 8.03 (d, 1H), 7.84 (m, 1H), 7.72 (m, 1H), 7.58-7.44 (m, 5H), 7.22 (d, 1H), 6.79 (d, 1H), 6.73 (s, 1H), 3.87 (s, 2H), 3.09 (s, 3H). MS(ES): 454 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-80% EtOAc/hexanes)

Sources & evidence

ORD record
ord-922f428fa70c4db8a8752f90fe63d339
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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