Dimethyl Sulfoxide → 2-(3-Bromo-1H-pyrrol-1-yl)pyridine

HRID 2222264Notes

Reaction equation

HRID 2222264 reaction equation
[Br:1][Si](C)(C)C.CS(C)=O.[N:10]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11]1.O>CC#N.CCOC(C)=O>[Br:1][C:12]1[CH:13]=[CH:14][N:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 76113BromotrimethylsilaneHCID 7365572-(1H-Pyrrol-1-yl)pyridine

Product 1

HCID 534231772-(3-Bromo-1H-pyrrol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Bromotrimethylsilane (10.9 mL, 84 mmol) was added to DMSO (5.7 mL, 84 mmol) in MeCN (200 mL) at 0° C. After stirring for 10 min, 2-(1H-pyrrol-1-yl)pyridine (10 g, 70 mmol) in MeCN (50 mL) was added. The reaction mixture was stirred at 0° C. and allowed to reach rt over 3 h. H2O (150 mL) and EtOAc (150 mL) were added and the reaction mixture was shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (3×150 mL). The combine organic layers were dried over Na2SO4 and concentrated to a brown oil. LCMS indicated good conversion to 2-(3-bromo-1H-pyrrol-1-yl)pyridine and this was used without further purification. (MS (ESI) 224 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at 0° C.
  2. waitto reach rt over 3 h
  3. stirringthe reaction mixture was shaken
  4. customthe EtOAc layer was separated
  5. stirringthe aqueous layer shaken with EtOAc (3×150 mL)
  6. dry with materialThe combine organic layers were dried over Na2SO4
  7. concentrationconcentrated to a brown oil
  8. customthis was used without further purification

Sources & evidence

ORD record
ord-24748e6ee29b4ebabc9fb6c3b6404658
Source dataset
uspto-grants-2008_05
Patent number
US07371767B2

Reaction notes

Loading…