Phenol → Ethyl 3-(phenoxymethyl)imidazo[1,2-a]pyridine-2-carboxylate

HRID 1184197Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl.Cl[CH2:12][C:13]1[N:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]2=[N:15][C:14]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(N(CC)CC)C>CN(C=O)C.O>[O:7]([CH2:12][C:13]1[N:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]2=[N:15][C:14]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of a mixture of phenol (2.20 g) and sodium hydride (95 wt %, 500 mg) in DMF (40 ml) was added dropwise to a solution of ethyl 3-(chloromethyl)imidazo[1,2-a]pyridine-2-carboxylate hydrochloride (3.5 g) in DMF (50 ml) at 0° C. Triethylamine (2.7 ml) was added at the same temperature over 30 min. The reaction mixture was stirred at 50° C. for 3 hr, and the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (6:1) was concentrated under reduced pressure to give the object product (1.5 g).

Workup

extractionextracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
washa fraction eluted with ethyl acetate-hexane (6:1)
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-98db07bc3aa84b21bea670019ab23423
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664380B2

Reaction notes

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