Water → (2,5-Dimethylpyrrol-1-yl)-5-bromobenzofuran-2-yl-methanone

HRID 1860622Notes

Reaction equation

HRID 1860622 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6]([CH3:9])=[CH:7][CH:8]=1.[Br:10][C:11]1[CH:12]=[CH:13][C:14]2[O:18][C:17]([C:19](Cl)=[O:20])=[CH:16][C:15]=2[CH:22]=1.O>C1COCC1.C(OCC)(=O)C>[CH3:3][C:4]1[N:5]([C:19]([C:17]2[O:18][C:14]3[CH:13]=[CH:12][C:11]([Br:10])=[CH:22][C:15]=3[CH:16]=2)=[O:20])[C:6]([CH3:9])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 122652,5-DimethylpyrroleHCID 24758Sodium hydrideHCID 27955345-Bromobenzo[b]furan-2-carbonyl chloride

Product 1

HCID 9927004(2,5-Dimethylpyrrol-1-yl)-5-bromobenzofuran-2-yl-methanoneYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

0.3 g of sodium hydride (60% suspension in paraffin oil) is introduced into 10 ml of THF and 0.5 mL [sic] of 2,5-dimethylpyrrole in 10 ml of THF is added dropwise (5 minutes). After stirring at 50° C. for 1 hour, a reddish suspension is present. 1.3 g of 5-bromobenzofuran-2-carbonyl chloride in 10 ml of THF is [sic] added dropwise at 25° C. (5 minutes) and the mixture is subsequently stirred for 2 hours. The addition of 100 ml of completely deionized water and 100 ml of ethyl acetate follows. The separated organic phase was additionally washed 2× with 100 ml of water and concentrated in vacuo. After chromatography on silica gel (eluent heptane/ethyl acetate 4:1), the residual oil gives 700 mg of yellow crystals (yield 44%), m.p. 115-116°.

Workup

  1. additionis added dropwise (5 minutes)
  2. additionadded dropwise at 25° C. (5 minutes)
  3. stirringthe mixture is subsequently stirred for 2 hours
  4. washThe separated organic phase was additionally washed 2× with 100 ml of water
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac4e658717914856a5b3bc3aa164c6b2
Source dataset
uspto-grants-2003_03
Patent number
US06531503B1

Reaction notes

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