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

HRID 1453540Notes

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 of a 1 M solution of diisobutylaluminium hydride in tetrahydrofuran are added dropwise within 20 minutes to a solution of 13.5 g of dimethyl 2-bromo-1-(2-butyn-1-yl)-1H-imidazole-4,5-dicarboxylate in 220 ml of tetrahydrofuran under an argon atmosphere at −70° C. The mixture is stirred for a further four hours at −70° C., then 20 ml of a mixture of 1 M hydrochloric acid and tetrahydrofuran are added dropwise. After heating to ambient temperature approx. 200 ml of water are added and the mixture is extracted three times with 70 ml of ethyl acetate. The combined extracts are dried and evaporated down. The crude product thus obtained is purified by column chromatography through silica gel with petroleum ether/ethyl acetate (4:1->1:1) as eluant.

Workup

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

Sources & evidence

ORD record: ord-a93d0b1832a04492bfb8c25227319efe
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476671B2

Reaction notes

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