Sodium Hydroxide → HCID 66585012, compound

HRID 1629979Notes

Reaction equation

HRID 1629979 reaction equation
[Cl: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]=[C:11]([F:15])[CH:10]=1.[OH-].[Na+].[C:18]([O:22][C:23](=[O:28])[NH:24][CH2:25][CH2:26]Br)([CH3:21])([CH3:20])[CH3:19]>C(#N)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:18]([O:22][C:23](=[O:28])[NH:24][CH2:25][CH2:26][N:6]1[CH:5]=[C:4]([C:7]#[N:8])[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[C:2]1[Cl:1])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66584592HCID 66584592, compound

Product 1

HCID 66585012HCID 66585012, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 39.5 g (179 mmol) of 5-chloro-4-(3-fluorophenyl)-1H-pyrrole-3-carbonitrile in 450 ml of acetonitrile are added 14.3 g (358 mmol) of powdered sodium hydroxide and 2.43 g (7.1 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for 30 minutes, 48.1 g (214 mmol) of tert-butyl(2-bromoethyl)-carbamate (CAS 39684-80-5) are then added and the mixture is then stirred for 17 hours at reflux. After cooling, the solvent is evaporated off under reduced pressure, and the residue is taken up in ethyl acetate. The organic phase is then washed with saturated sodium chloride solution and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give 47.3 g of tert-butyl{2-[2-chloro-4-cyano-3-(3-fluorophenyl)-1H-pyrrol-1-yl]ethyl}-carbamate in the form of a beige-coloured powder after triturating in 150 ml of diisopropyl ether, filtering off and drying.

Workup

  1. stirringthe mixture is then stirred for 17 hours
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. customthe solvent is evaporated off under reduced pressure
  5. washThe organic phase is then washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-cf5e77d0efa24686a0ed22f84d3fbd14
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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