Boron tribromide → Awd 12-281

HRID 1069024

Reaction equation

HRID 1069024 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[NH:8][C:9](=[O:31])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:21]C)[CH:19]=2)[N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:13]=1)=[O:11].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[NH:8][C:9](=[O:31])[C:10]([C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([OH:21])[CH:19]=2)[N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 11123551N-(3,5-dichloropyridin-4-yl)-2-[1-(4-fluorobenzyl)-5-methoxyindol-3-yl]-2-oxoacetamide

Product 1

HCID 6918428Awd 12-281

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.4 g of N-(3,5-dichloropyridin-4-yl)-2-[1-(4-fluorobenzyl)-5-methoxyindol-3-yl]-2-oxoacetamide (3 mmol) is dissolved in 100 ml of dichloromethane. The solution is heated to reflux and treated with a solution of 14 mmol of BBr3 in 15 ml of dichloromethane with stirring. The reaction mixture is refluxed for 3 hours. After cooling, the solution is intensively stirred for 3 hours at 20° C. with 200 ml of an aqueous sodium hydrogencarbonate solution. The product crystallizes out, it is isolated, dried at 60° C. and recrystallized from 80 ml of ethanol.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture is refluxed for 3 hours
  4. temperatureAfter cooling
  5. customThe product crystallizes out
  6. customit is isolated
  7. customdried at 60° C.
  8. customrecrystallized from 80 ml of ethanol

Sources & evidence

ORD record
ord-7bef48c427e3463b9b0763a43fd339d6
Source dataset
uspto-grants-2001_06
Patent number
US06251923B1

Linked notes

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