Sodium hydride → HCID 66924824, compound

HRID 554179Notes

Reaction equation

HRID 554179 reaction equation
FC1C=CC(C(=O)CBr)=CC=1.[C:12]([CH:14]([CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:13].FC1C=CC(C2NC=C(C(OCC)=O)C=2)=CC=1.[H-].[Na+].[F:49][C:50]([F:62])([F:61])[C:51]1[CH:56]=[CH:55][C:54]([S:57](Cl)(=[O:59])=[O:58])=[CH:53][CH:52]=1>CN(C)C=O.O>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[N:13]([S:57]([C:54]3[CH:53]=[CH:52][C:51]([C:50]([F:49])([F:61])[F:62])=[CH:56][CH:55]=3)(=[O:59])=[O:58])[CH:12]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:20]=2)=[CH:24][CH:25]=1

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 19979312HCID 19979312, compoundHCID 66924929HCID 66924929, compound2×

Product 1

HCID 66924824HCID 66924824, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Using 4-fluorophenacyl bromide instead of phenacyl bromide, a procedure as in Reference Example 1 was performed to synthesize ethyl 2-cyano-4-(4-fluorophenyl)-4-oxobutanoate, and procedures as in Reference Examples 2 and 3 were performed to synthesize ethyl 5-(4-fluorophenyl)-1H-pyrrole-3-carboxylate. Sodium hydride (60% in oil, 0.28 g) was added to a solution (20 mL) of ethyl 5-(4-fluorophenyl)-1H-pyrrole-3-carboxylate (1.49 g) in N,N-dimethylformamide under ice-cooling. The mixture was stirred at the same temperature for 15 min, 4-trifluoromethylbenzenesulfonyl chloride (1.85 g) was added, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:2) to give the title compound as crystals (yield 1.80 g, 64%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 3 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:2)

Sources & evidence

ORD record
ord-1bc9802594c24794987cfaf4b422d21b
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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