Dichloromethane → Ethyl 3-({[(1,1-dimethylethyl)(diethyl)silyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carboxylate

HRID 406277Notes

Reaction equation

[OH:1][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[N:5][CH:4]=1.[C:17]([Si:21](Cl)([CH3:23])C)([CH3:20])([CH3:19])[CH3:18].C(N([CH2:30][CH3:31])CC)C.[CH2:32](Cl)Cl>CN(C)C1C=CN=CC=1>[CH3:18][C:17]([Si:21]([CH2:30][CH3:31])([CH2:23][CH3:32])[O:1][CH2:2][C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6]2=[N:5][CH:4]=1)([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of ethyl 3-(hydroxymethyl)imidazo[1,2-a]pyridine-8-carboxylate (2.7 g, 12.26 mmol) in DCM (100 mL) under nitrogen was added tert-butylchlorodimethyl silane (4 g, 26.5 mmol), 4-dimethylamino pyridine (0.32 g, 2.62 mmol) and triethylamine (3 mL, 21.52 mmol) and the reaction mixture heated at 50° C. under nitrogen for 16 hours. The mixture was concentrated in vacuo and the residue was dissolved in DCM and purified on a silica cartridge (100 g) using a 0-30% methanol-DCM gradient over 60 mins. The product containing fractions were combined and evaporated in vacuo to give the title compound as an off-white solid (4.174 g).

Workup

concentrationThe mixture was concentrated in vacuo
dissolutionthe residue was dissolved in DCM
custompurified on a silica cartridge (100 g)
customover 60 mins
additionThe product containing fractions
customevaporated in vacuo

Sources & evidence

ORD record: ord-2feeb63d068a46b2acadd1b0c2aaa593
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754101B2

Reaction notes

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