Methanol → (6-Methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 623955Notes

Reaction equation

HRID 623955 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)=[O:9])=[CH:4][N:3]=1.[CH3:16][OH:17]>>[CH3:16][O:17][C:2]1[N:3]=[CH:4][C:5]([C:8]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)=[O:9])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 120166732-Chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine2×

Product 1

HCID 86715443(6-Methoxypyridin-3-yl)(1-methyl-1H-imidazol-5-yl)methanone

Conditions

Temperature
75 °C

Procedure

In a 50-mL round-bottom flask was placed a solution of Na (260 mg, 11.3 mmol) in methanol (15 mL) and the solution was stirred for 30 minutes at room temperature. Then 2-chloro-5-[(1-methyl-1H-imidazol-5-yl)carbonyl]pyridine (250 mg, 1.13 mmol, Intermediate 4, step c) was added. The resulting mixture was stirred for 4 hours at 75° C. and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, 100:0-20:1 CH2Cl2:MeOH) to give the title compound as a light yellow solid.

Workup

  1. customIn a 50-mL round-bottom flask was placed
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash column chromatography (silica gel, 100:0-20:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-d531ce4ecd964391819bc66ded6e5923
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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