Water → HCID 67396230, compound

HRID 1426677Notes

Reaction equation

HRID 1426677 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C:16]([C:17]3[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][C:14]([CH2:24][N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#N.C[Li].[OH2:36].[CH2:37](OCC)C>>[C:1]([C:3]1[CH:4]=[C:5]([S:9]([N:12]2[C:16]([C:17]3[C:18]([F:23])=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:15][C:14]([CH2:24][N:25]([CH3:33])[C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[CH:13]2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)(=[O:36])[CH3:37]

Participants

5

Reactant 4

HCID 962WaterHCID 3283Diethyl Ether2×HCID 67398625HCID 67398625, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 67396230HCID 67396230, compoundYield 25%

Procedure

To a solution of tert-butyl ({1-[(3-cyanophenyl)sulfonyl]-5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl}methyl)methylcarbamate (431 mg) in diethyl ether (4 mL) was added a 1.0 mol/L solution (2.4 mL) of methyllithium in diethyl ether at −78° C., and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a brown oil (yield 110 mg, 25%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-9210abf4277b42e79eec103b91ef16cf
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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