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

HRID 734896Notes

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

Participants

Conditions

Temperature: 0 °C

Procedure

0.06 mL (0.75 mmol) of methanesulfonic acid chloride was added dropwise at 0° C. to a solution of 167 mg (0.50 mmol) of 2-{4-[5-(4-chlorophenyl)pyridin-2-ylethynyl]phenyl}ethanol and 0.08 mL (1.00 mmol) of pyridine in 5 mL of DCM and the mixture was then stirred for I hour at 0° C. It was combined again with pyridine (0.08 mL) and methanesulfonic acid chloride (0.06 mL) and stirred for 1 hour at RT. Then it was combined with 0.14 mL (1.00 mmol) of triethylamine and after 20 minutes at RT diluted with ice water. The organic phase was separated off, dried over magnesium sulfate, filtered, and the solvent was eliminated in vacuo. Yield: 185 mg (90% of theoretical); C22H18ClNO3S (M=411.902); calc.: molpeak (M+H)+:412/414 (Cl); found: molpeak (M+H)+:412/414 (Cl); HPLC-MS: 6.27 minutes (method H).

Workup

stirringstirred for 1 hour at RT
customThe organic phase was separated off
dry with materialdried over magnesium sulfate
filtrationfiltered
custom6.27 minutes (method H)

Sources & evidence

ORD record: ord-562e00ed531d451f93b4ee974bbba072
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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