Methanol → methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate

HRID 2277499

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][N:10]=2)[N:6]=[CH:5]1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].CO>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][N:10]=2)[N:6]=[CH:5]1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of methyl 2-[1-(2-hydroxyethyl)-1H-imidazol-4-yl]pyridine-4-carboxylate (500 mg, 2 mmol) in DCM (10 mL) was added TEA (255 mg, 2.5 mmol) followed by drop-wise addition of a solution of methanesulfonyl chloride (255 mg, 2.22 mmol) in DCM (2 mL). The solution was stirred at 0° C. for 1 hr and then allowed to warm to r.t. where stirring was continued for 1 hr. MeOH (1 mL) was then added and stirring was continued for 30 min. The solution was diluted with DCM (50 mL), washed with water (50 mL), dried (MgSO4), filtered, and concentrated to give the title compound as an oily residue (649 mg).

Workup

temperatureto warm to r.t. where
stirringstirring
waitwas continued for 1 hr
stirringstirring
waitwas continued for 30 min
washwashed with water (50 mL)
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-afc6dc5deaaa4ea78b218f44966dd109
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133166B2

Linked notes

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