Pyridine → HCID 54356073, compound

HRID 2106669Notes

Reaction equation

HRID 2106669 reaction equation
[CH:1]1([C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])([C:6]2[N:7]([CH3:11])[CH:8]=[CH:9][CH:10]=2)O)[CH2:3][CH2:2]1.[Br:19][Si](C)(C)C.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:19][CH2:3][CH2:2][CH:1]=[C:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18])[C:6]1[N:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 76113BromotrimethylsilaneHCID 516892Sodium BicarbonateHCID 23048938HCID 23048938, compound

Product 1

HCID 54356073HCID 54356073, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Cyclopropyl-(2-methylphenyl)-(N-methylpyrrol-2-yl)methanol (9.9 g, 0.041 mole) was dissolved in dichloromethane (250 ml) and cooled to -70° C. under nitrogen. Bromotrimethylsilane (6.4 g, 0.042 mole) in dichloromethane (250 ml) was added within 30 min. The reaction mixture was stirred at -70° C. for another 90 min. Pyridine (3.5 ml) was added and when the mixture had reached room temperature, saturated sodium bicarbonate solution (100 ml) was added. The phases were separated and the organic phase was dried (MgSO4) and evaporated leaving the title compound as an oil (10.9 g).

Workup

  1. customhad reached room temperature
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-19eae20be8c344c48fe79ff9234746b5
Source dataset
uspto-grants-1990_06
Patent number
US04931450

Reaction notes

Loading…