Dimethylformamide → methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

HRID 1409425Notes

Reaction equation

Br[C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.C([Mg]Cl)(C)C.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:2]1[N:3]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)=[O:28]

Participants

Conditions

Temperature: -40 °C

Procedure

Into a flask containing methyl 2-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate (5 g, 14.9 mmol) in THF (20 ml), 2 M solution of i-PrMgCl in THF (22.4 ml, 44.9 mmol) was added at −40° C. under nitrogen atmosphere. The resulting mixture was allowed to stir for 10 min at −40° C. and cooled to −78° C. The reaction mixture was treated with DMF (7.29 ml, 89.8 mmol) and slowly warmed to RT. The mixture was stirred for 1 h at RT and quenched with saturated aqueous solution of NaHCO3. The crude was extracted with EtOAc. The organic layer was concentrated under reduced pressure. Yield 3 g. LC-MS: [M+1]=285.15.

Workup

additionwas added at −40° C. under nitrogen atmosphere
temperaturecooled to −78° C
temperatureslowly warmed to RT
stirringThe mixture was stirred for 1 h at RT
customquenched with saturated aqueous solution of NaHCO3
extractionThe crude was extracted with EtOAc
concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-c3cd757b25864047a5361c11220083db
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921378B2

Reaction notes

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