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Ethyl 4-methyl-1H-pyrrole-2-carboxylate → 1-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2272972
Notes
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Reaction equation

HRID 2272972 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].[K].CC(C)([O-])C.Br[CH2:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=1)=[O:21]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]([C:22]2[CH:23]=[N:24][N:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=2)=[O:21])[CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylateHCID 50987170Potassium tertbutoxideHCID 898260822-bromo-1-(1-tert-butyl-1H-pyrazol-4-yl)-ethanone

Product 1

HCID 898261431-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

To a suspension of 229 mg (1.50 mmol) 4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester in 3.7 ml DMF is added 185 mg (1.65 mmol) potassium-tertbutoxide portionwise under nitrogen. The mixture is stirred for 30 minutes at room temperature and cooled to 0° C. Then 367 mg (1.50 mmol) 2-bromo-1-(1-tert-butyl-1H-pyrazol-4-yl)-ethanone is added. The mixture is stirred for 1 hour at 0° C. and for 30 minutes at room temperature. The reaction mixture is partitioned between dichloromethane and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate to afford 1-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as yellow oil; HPLC/MS 2.82 min (B), [M+H] 318.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe mixture is stirred for 1 hour at 0° C. and for 30 minutes at room temperature
  3. customThe reaction mixture is partitioned between dichloromethane and water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-e6d361df7c904b3282ccacbc6c844387
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09120805B2

Reaction notes

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