Sodium Bicarbonate → 2-Bromo-3-(3-methyl-2-buten-1-yl)-3,5-dihydro-imidazo[4,5-c]pyridin-4-one

HRID 230105Notes

Reaction equation

CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[Br:16][C:17]1[N:27]([CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[C:20]2[C:21](=[O:26])[NH:22][CH2:23][CH:24](O)[C:19]=2[N:18]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl.O1CCCC1>[Br:16][C:17]1[N:27]([CH2:28][CH:29]=[C:30]([CH3:32])[CH3:31])[C:20]2[C:21](=[O:26])[NH:22][CH:23]=[CH:24][C:19]=2[N:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.55 g Burgess reagent (methoxycarbonylsulphamoyl-triethylammonium-N-betaine) are added to 1.60 g of 2-bromo-7-hydroxy-3-(3-methyl-2-buten-1-yl)-3,5,6,7-tetrahydro-imidazo[4,5-c]pyridin-4-one in 20 ml methylene chloride and 4 ml of tetrahydrofuran. The reaction mixture is stirred for eight hours at 60° C., then another 0.3 equivalents Burgess reagent is added. After a further two hours the cooled reaction mixture is combined with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases are dried over magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with methylene chloride/methanol (1:0 to 10:1) as eluant.

Workup

customAfter a further two hours the cooled reaction mixture
extractionextracted with ethyl acetate
dry with materialThe combined organic phases are dried over magnesium sulphate
customevaporated down
customThe flask residue is chromatographed through a silica gel column with methylene chloride/methanol (1:0 to 10:1) as eluant

Sources & evidence

ORD record: ord-a847a26f40c841e7964c1c40150cf9e7
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566707B2

Reaction notes

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