Sodium Hydroxide → HCID 66584145, compound

HRID 1629995Notes

Reaction equation

HRID 1629995 reaction equation
[Cl:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=1.[OH-].[Na+].[C:21]([O:25][C:26](=[O:31])[NH:27][CH2:28][CH2:29]Br)([CH3:24])([CH3:23])[CH3:22]>C(#N)C.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:21]([O:25][C:26]([NH:27][CH2:28][CH2:29][N:6]1[C:2]([Cl:1])=[C:3]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)[C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:5]1)=[O:31])([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66584709HCID 66584709, compound

Product 1

HCID 66584145HCID 66584145, compoundYield 92.9%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 9.38 g (36.0 mmol) of methyl 5-chloro-4-(3-cyano-phenyl)-1H-pyrrole-3-carboxylate in 60 ml of acetonitrile are added 2.88 g (72.0 mmol) of powdered sodium hydroxide and 0.49 g (1.4 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 9.68 g (43.2 mmol) of tert-butyl(2-bromoethyl)carbamate (CAS 39684-80-5), and the mixture is then stirred for 6 hours at reflux. After cooling, the mixture is taken up in 250 ml of water and the product is extracted with ethyl acetate. The organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give an orange-coloured oil, which is purified by chromatography on a column of 150 g of silica gel, eluting with a mixture of 2% methanol in dichloromethane, to give 13.5 g of methyl 1-(2-tert-butyloxycarbonylaminoethyl)-5-chloro-4-(3-cyanophenyl)-1H-pyrrole-3-carboxylate in the form of a yellow oil.

Workup

  1. stirringthe mixture is then stirred for 6 hours
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. extractionthe product is extracted with ethyl acetate
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent is evaporated off under reduced pressure
  7. customto give an orange-coloured oil, which
  8. customis purified by chromatography on a column of 150 g of silica gel
  9. washeluting with a mixture of 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-c7ef38432fef46dcb31339f7a4f77ed8
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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