Dichloromethane → HCID 22418011, compound

HRID 1720287Notes

Reaction equation

HRID 1720287 reaction equation
ClCCl.B(Br)(Br)Br.[CH3:8][O:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]3=[N:30][CH:31]=[CH:32][C:33]([CH3:34])=[C:28]3[N:27]=[C:26]2[CH2:35][O:36]C)=[CH:20][CH:19]=1)=[O:11]>CO>[OH:36][CH2:35][C:26]1[N:25]([CH2:24][C:21]2[CH:22]=[CH:23][C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:10]([O:9][CH3:8])=[O:11])=[CH:19][CH:20]=2)[C:29]2=[N:30][CH:31]=[CH:32][C:33]([CH3:34])=[C:28]2[N:27]=1

Participants

5

Reactant 3

HCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 19014342HCID 19014342, compound

Product 1

HCID 22418011HCID 22418011, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 ml (50 mmol) of a dichloromethane solution of 1M boron tribromide was added little by little dropwise to 100 ml of a dichloromethane solution of 3.3 g (8.2 mmol) of 3-[(2'-methoxycarbonyl-biphenyl-4-yl) methyl]-2-methoxymethyl-7-methyl-3H-imidazo[4,5-b]pyridine, while stirred and cooled with ice. The mixture was further stirred at a room temperature for 12 hours. Methanol was added dropwise to the product mixture, while stirred and cooled with ice, and the solvent was distilled out at a reduced pressure. The residue was mixed with water and neutralized with sodium bicarbonate. It was weakly acidified with acetic acid and decanted to remove the water. Methanol was added to the residue and distilled out at a reduced pressure. It was re-crystallized from ethanol-isopropylether to obtain 2.4 g of the intended compound.

Workup

  1. temperaturecooled with ice
  2. stirringThe mixture was further stirred at a room temperature for 12 hours
  3. stirringwhile stirred
  4. temperaturecooled with ice
  5. distillationthe solvent was distilled out at a reduced pressure
  6. additionThe residue was mixed with water and neutralized with sodium bicarbonate
  7. customdecanted
  8. customto remove the water
  9. additionMethanol was added to the residue
  10. distillationdistilled out at a reduced pressure
  11. customIt was re-crystallized from ethanol-isopropylether

Sources & evidence

ORD record
ord-a66d5ae5895b48429a23089bc8be30ea
Source dataset
uspto-grants-1996_04
Patent number
US05506238

Reaction notes

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