Sodium Hydroxide → HCID 66585013, compound

HRID 1630003Notes

Reaction equation

HRID 1630003 reaction equation
[F:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]#[N:8])[C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+].[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25]Br)([CH3:20])([CH3:19])[CH3:18]>C(#N)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:17]([O:21][C:22](=[O:27])[NH:23][CH2:24][CH2:25][N:6]1[CH:5]=[C:4]([C:7]#[N:8])[C:3]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:2]1[F:1])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66584732HCID 66584732, compound

Product 1

HCID 66585013HCID 66585013, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3.75 g (20.1 mmol) of 5-fluoro-4-phenyl-1H-pyrrole-3-carbonitrile in 101 ml of acetonitrile are added 1.6 g (40 mmol) of finely ground sodium hydroxide and 0.27 g (0.81 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 5.42 g (24.2 mmol) of tert-butyl(2-bromoethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 18 hours at 90° C. After cooling, the solvent is evaporated off under reduced pressure and the residue is taken up in twice 125 ml of water. The product is extracted with ethyl acetate. The organic phase is then washed with saturated aqueous sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a column of silica gel, eluting with a mixture of 15 to 50% ethyl acetate in cyclohexane, to give 2.5 g of tert-butyl{2-[4-cyano-2-fluoro-3-phenyl-1H-pyrrol-1-yl]ethyl}carbamate in the form of a brown oil.

Workup

  1. stirringthe mixture is then stirred for 18 hours at 90° C
  2. temperatureAfter cooling
  3. customthe solvent is evaporated off under reduced pressure
  4. extractionThe product is extracted with ethyl acetate
  5. washThe organic phase is then washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure
  8. customThe residue is purified by chromatography on a column of silica gel
  9. washeluting with a mixture of 15 to 50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-740439ab98404a7598aa7fae9d697f59
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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