Methanesulfonyl chloride → 2-(5-Cyanopyridin-2-yl)ethyl methanesulfonate

HRID 1466048Notes

Reaction equation

HRID 1466048 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C(Cl)Cl>[CH3:12][S:13]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]#[N:11])=[CH:8][N:9]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19045350HCID 19045350, compound

Product 1

HCID 895250142-(5-Cyanopyridin-2-yl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NaBH4 (2.5 g, 67 mmol) was added in small portions to a solution of 6-(2-oxoethyl)pyridine-3-carbonitrile (5.0 g, crude) in 80 mL of MeOH at 0° C. The mixture was stirred at room temperature for 30 minutes and poured to 50 mL of water. The mixture was extracted with EtOAc (100 mL×5) and the combined organic layer was condensed. The residue was purified by flash chromatography to afford 6-(2-hydroxyethyl)pyridine-3-carbonitrile. TEA (2.1 g, 21 mmol) was added drop wise to a solution of 6-(2-hydroxyethyl)pyridine-3-carbonitrile (3.0 g, 20 mmol) and MsCl (2.3 g, 20 mmol) in 200 mL of DCM at 0° C. The mixture was stirred at RT for 30 minutes and washed with water and brine, dried over anhydrous Na2SO4 and condensed under vacuum below 30° C. to afford the title compound which was used immediately without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous Na2SO4 and condensed under vacuum below 30° C.

Sources & evidence

ORD record
ord-a4e1a2066f0143e985cc7b84b5db4397
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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