Benzyl Bromide → HCID 67231887, compound

HRID 1511912Notes

Reaction equation

HRID 1511912 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[N:8]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:6].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH3:3][O:4][C:5]([C:7]1[N:8]([N:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:9]=[CH:10][CH:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 59197204HCID 59197204, compound

Product 1

HCID 67231887HCID 67231887, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (105 mg, 2.24 mmol, 60% purity in mineral oil) was added in one portion to a stirred, ice/water-cooled solution of 1-tert-butoxycarbonylamino-1H-pyrrole-2-carboxylic acid methyl ester (448 mg, 1.86 mmol) and benzyl bromide (267 μL, 2.24 mmol) in DMF (8 mL); the mixture was stirred in the cold bath for 60 min, at which time TLC showed complete disappearance of starting material; then poured into diluted, cold ammonium chloride solution to quench, followed by extraction with EtOAc, then washed with water, and brine; the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was silica gel column purified to give the desired product (530 mg) as a clear oil. ESI (m/z): 353 (M+Na)+.

Workup

  1. additionthen poured
  2. additioninto diluted
  3. customcold ammonium chloride solution to quench
  4. extractionfollowed by extraction with EtOAc
  5. washwashed with water, and brine
  6. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified

Sources & evidence

ORD record
ord-1ebd6382d2bc402d9d814d461057dbe9
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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