Water → 2-[1-(4-Cyanopyridin-2-yl)pyrazol-4-yl]ethyl methanesulfonate

HRID 878713

Reaction equation

HRID 878713 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][N:10]=2)[CH:8]=1.CCN(CC)CC.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C(Cl)Cl>[CH3:24][S:25]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[N:6][N:7]([C:9]2[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][N:10]=2)[CH:8]=1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867256632-[4-(2-Hydroxyethyl)pyrazol-1-yl]pyridine-4-carbonitrile

Product 1

HCID 867256652-[1-(4-Cyanopyridin-2-yl)pyrazol-4-yl]ethyl methanesulfonateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-[4-(2-hydroxyethyl)pyrazol-1-yl]pyridine-4-carbonitrile (700 mg, 3.3 mmol), Et3N (670 mg, 6.6 mmol) in DCM (15 mL) was added MeSO2Cl (410 mg, 3.6 mmoL) at 0° C., the mixture was then stirred for 2 hours at room temperature, water was added and extracted with DCM and concentrated give the title compound (830 mg, 87%). [M+H] Calc'd for C12H12N4O3S, 293; Found, 293.

Workup

  1. extractionextracted with DCM
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-9163bf5970ff46958678ead4f7f6e0a3
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Linked notes

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