Water → HCID 71279213, compound

HRID 1621162Notes

Reaction equation

HRID 1621162 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[N:10]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:9]=[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:7]=1.O>CS(C)=O>[C:17]1([C:8]2[N:7]=[C:6]([CH2:5][C:1]#[N:2])[N:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)[N:9]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9032Potassium CyanideHCID 86677494HCID 86677494, compound

Product 1

HCID 71279213HCID 71279213, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of potassium cyanide (30.7 mg, 472 μmol) and 3-(5-(bromomethyl)-3-phenyl-1H-1,2,4-triazol-1-yl)pyridine (124 mg, 393 μmol) in DMSO (3 mL) was stirred at RT for 2 h. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic phase was washed with water and brine, dried, filtrated and evaporated. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as light brown solid (47 mg with 80% purity, 180 μmol, 36.6%).

Workup

  1. extractionextracted with ethyl acetate (2×25 mL)
  2. washThe combined organic phase was washed with water and brine
  3. customdried
  4. filtrationfiltrated
  5. customevaporated
  6. customThe product was obtained
  7. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-03728c5bc44a46788a0cd68f685cfb1b
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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