Water → HCID 59477905, compound

HRID 570857Notes

Reaction equation

HRID 570857 reaction equation
[Si]([O:18][CH2:19][C:20]1[C:21]([C:25]#[N:26])=[CH:22][NH:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:27]([O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][C:34](F)=[CH:33][CH:32]=1)[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:27]([O:29][C:30](=[O:38])[C:31]1[CH:36]=[CH:35][C:34]([N:23]2[CH:24]=[C:20]([CH2:19][OH:18])[C:21]([C:25]#[N:26])=[CH:22]2)=[CH:33][CH:32]=1)[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 59477768HCID 59477768, compound

Product 1

HCID 59477905HCID 59477905, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A suspension of 4-(tert-butyldiphenylsilanyloxymethyl)-1H-pyrrole-3-carbonitrile (0.3 g), 4-fluorobenzoic acid ethyl ester (0.35 g) and cesium carbonate (0.81 g) in N,N-dimethylformamide (2 mL) was stirred at 70° C. overnight. To this reaction mixture was added water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=80/20-30/70) to give the title compound (0.0310 g).

Workup

  1. extractionthis mixture was extracted with ethyl acetate
  2. washThis organic layer was washed with water and brine
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=80/20-30/70)

Sources & evidence

ORD record
ord-990a6f3655344239a540d7237260cce0
Source dataset
uspto-grants-2015_05
Patent number
US09023882B2

Reaction notes

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