Hydrochloric Acid → methyl 2-bromo-3-(2-butyn-1-yl)-5-formyl-3H-imidazole-4-carboxylate

HRID 2214454Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([C:17](OC)=[O:18])[N:16]=1.Cl.O>O1CCCC1>[Br:11][C:12]1[N:13]([CH2:25][C:26]#[C:27][CH3:28])[C:14]([C:21]([O:23][CH3:24])=[O:22])=[C:15]([CH:17]=[O:18])[N:16]=1

Participants

Conditions

Temperature: -70 °C

Procedure

43 ml (43 mmol) of a 1 molar solution of diisobutyl-aluminium hydride in tetrahydrofuran within 20 minutes were added dropwise to a solution of 13.5 g (42.84 mmol) of dimethyl 2-bromo-1-(but-2-ynyl)-1H-imidazol-4,5-dicarboxylate in 220 ml of tetrahydrofuran under an argon atmosphere at −70° C. The mixture was stirred for a further 4 hours at −70° C., then 20 ml of a mixture of 1M hydrochloric acid and tetrahydrofuran were added dropwise. After heating to ambient temperature approx. 200 ml of water were added and the mixture was extracted three times with 70 ml of ethyl acetate. The extracts were dried and evaporated down, and the crude product thus obtained was purified by column chromatography (silica gel; eluant:petroleum ether with 20–50% ethyl acetate).

Workup

temperatureAfter heating to ambient temperature approx
extractionthe mixture was extracted three times with 70 ml of ethyl acetate
customThe extracts were dried
customevaporated down

Sources & evidence

ORD record: ord-6a51d612ded8452e81368a4cd5532f85
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109192B2

Reaction notes

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