Triethylamine → HCID 86680633, compound

HRID 1497468Notes

Reaction equation

HRID 1497468 reaction equation
[OH:1][CH:2]([C:5]1[N:10]=[CH:9][C:8]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])=[CH:7][CH:6]=1)[CH2:3][CH3:4].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C1COCC1>[CH3:26][S:27]([O:1][CH:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])=[CH:9][N:10]=1)[CH2:3][CH3:4])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86680632HCID 86680632, compound

Product 1

HCID 86680633HCID 86680633, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 2-(6-(1-hydroxypropyl)pyridin-3-yl)benzonitrile (0.05 g) in THF (3 mL) was added triethyl amine (0.042 g), the mixture was stirred for 5 minutes, and then methanesulfonyl chloride was added (0.47 g). The mixture was stirred at room temperature for 90 min. The reaction mixture was quenched with sodium bicarbonate and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate, filtered and concentrated to obtain 1-(5-(2-cyanophenyl)pyridin-2-yl)propyl methanesulfonate (0.050 g, 71% yield), which was used directly in the next step.

Workup

  1. stirringThe mixture was stirred at room temperature for 90 min
  2. customThe reaction mixture was quenched with sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e7c20fe38fd4b7aacfc226499c336dd
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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