Sodium Hydroxide → HCID 66584135, compound

HRID 1630025Notes

Reaction equation

HRID 1630025 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=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>[C:21]([O:25][C:26]([NH:27][CH2:28][CH2:29][N:6]1[C:2]([Br:1])=[C:3]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5]1)=[O:31])([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 66584943HCID 66584943, compound

Product 1

HCID 66584135HCID 66584135, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 39.6 g (127 mmol) of ethyl 5-bromo-4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in 275 ml of acetonitrile are added 10.1 g (253 mmol) of powdered sodium hydroxide and 1.7 g (5.1 mmol) of tetrabutylammonium hydrogen sulfate, and the mixture is stirred vigorously for a few minutes, followed by adding 34.1 g (152 mmol) of tert-butyl(2-bromoethyl)carbamate (CAS 39684-80-5), 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 solution is washed with saturated aqueous sodium chloride solution, the organic phase is then dried over sodium sulfate and the solvent is evaporated off under reduced pressure, to give a brown oil, which is crystallized from diisopropyl ether, to give 43 g of ethyl 1-(2-tert-butoxycarbonylaminoethyl)-5-bromo-4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in the form of a beige-coloured powder after 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 solution is washed with saturated aqueous sodium chloride solution
  6. dry with materialthe organic phase is then dried over sodium sulfate
  7. customthe solvent is evaporated off under reduced pressure
  8. customto give a brown oil, which
  9. customis crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-4684ff3d3aa84762a56b4f54d4bec4a5
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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