Pyridine → 2-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethyl methanesulfonate

HRID 734882Notes

Reaction equation

HRID 734882 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[CH:15][C:16]([C:19]#[C:20][C:21]3[CH:30]=[CH:29][C:24]([O:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:22]=3)=[N:17][CH:18]=2)=[CH:9][CH:8]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][S:2]([O:28][CH2:27][CH2:26][O:25][C:24]1[CH:23]=[CH:22][C:21]([C:20]#[C:19][C:16]2[CH:15]=[N:14][C:13]([C:10]3[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=3)=[CH:18][N:17]=2)=[CH:30][CH:29]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 690588142-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol

Product 1

HCID 866011392-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.62 mL (7.98 mmol) of methanesulfonic acid chloride was added dropwise at RT to a solution of 700 mg (2.00 mmol) of 2-{4-[5-(4-chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol and 0.65 mL (7.98 mmol) of pyridine in 20 mL of DCM and the mixture was then stirred overnight at RT. After the addition of another 0.33 mL (3.99 mmol) of pyridine and 0.32 mL (4.12 mmol) of methanesulfonic acid chloride, the reaction mixture was stirred for a further 2 hours at RT in the ultrasound bath. The solution was diluted with 30 mL DCM, and the organic phase was separated off, washed three times with 60 mL of water, and dried over magnesium sulfate. After the desiccant and solvent had been eliminated, the residue was purified by chromatography (silica gel, DCM). Yield: 600 mg (70% of theoretical); C21H17ClN2O4S (M=428.889); calc.: molpeak (M+H)+:429/431 (Cl); found: molpeak (M+H)+:429/431 (Cl); Rf value: 0.30 (silica gel, DCM/MeOH 9:1).

Workup

  1. stirringthe reaction mixture was stirred for a further 2 hours at RT in the ultrasound bath
  2. customthe organic phase was separated off
  3. washwashed three times with 60 mL of water
  4. dry with materialdried over magnesium sulfate
  5. customthe residue was purified by chromatography (silica gel, DCM)

Sources & evidence

ORD record
ord-50fd1c17ed094f2bb6cdc21cfdd0379b
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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