1-Bromo-2-butanone → HCID 89610332, compound

HRID 1507725Notes

Reaction equation

HRID 1507725 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH3:5].[CH2:7]([O:14][C:15]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([C:28](=[S:30])[NH2:29])[N:17]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:16]=1[C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCO>[CH2:7]([O:14][C:15]1[C:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([C:28]2[S:30][CH:2]=[C:3]([CH2:4][CH3:5])[N:29]=2)[N:17]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[C:16]=1[C:39]([O:41][CH2:42][CH3:43])=[O:40])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 89610299HCID 89610299, compound

Product 1

HCID 89610332HCID 89610332, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-bromobutan-2-one (24 μL, 0.21 mmol) and ethyl 3,4-bis(benzyloxy)-5-carbamothioyl-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (29) [prepared under standard conditions from UL1-079 and Lawesson reagent] (100 mg, 0.19 mmol) in EtOH (4 mL) was heated at 80° C. for 45 min. The volatiles were removed in vacuo and the product was purified by silica gel chromatography (12 g cartridge, 0-25% EtOAc in isohexane) to afford ethyl 3,4-bis(benzyloxy)-5-(4-ethylthiazol-2-yl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (30) (82 mg, 75%) as a yellow oil: m/z 569 (M+H)+ (ES+).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe product was purified by silica gel chromatography (12 g cartridge, 0-25% EtOAc in isohexane)

Sources & evidence

ORD record
ord-3594be74b5d144e399939c793071b210
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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