Cyanomethylenetributylphosphorane → Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 923454Notes

Reaction equation

HRID 923454 reaction equation
[OH:1][C:2]1[C:3]2[N:4]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[F:17][C:18]1[C:19]([CH2:24]O)=[N:20][CH:21]=[CH:22][CH:23]=1.C(P(=CC#N)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:17][C:18]1[C:19]([CH2:24][O:1][C:2]2[C:3]3[N:4]([C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([CH3:11])[N:10]=3)[CH:5]=[CH:6][CH:7]=2)=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 4622928CyanomethylenetributylphosphoraneHCID 19703803(3-Fluoropyridin-2-yl)methanolHCID 21717316Ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 86718211Ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylateYield 71.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2 g of ethyl 8-hydroxy-2-methylimidazo[1,2-a]pyridine-3-carboxylate, 2 g of (3-fluoropyridin-2-yl)methanol, 4 g of (tributylphosphoranyliden)acetonitrile, and 40 ml of toluene was stirred at 110° C. for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added thereto, and the precipitated solid was collected by filtration. The obtained residue was purified by silica gel column chromatography to obtain 2.15 g of ethyl 8-[(3-fluoropyridin-2-yl)methoxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, water
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b8173e177f74bd29ba9e7986e33d7a9
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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