Boron tribromide → N-(5-chloro(2-pyridyl)){6-[(4-cyanophenyl)-carbonylamino]3-hydroxyphenyl}carboxamide

HRID 514733Notes

Reaction equation

HRID 514733 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[CH:16]=[C:15]([O:17]C)[CH:14]=[CH:13][C:12]=2[NH:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)=[O:21])=[O:10])=[N:6][CH:7]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:12]([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=3)=[O:21])=[CH:13][CH:14]=[C:15]([OH:17])[CH:16]=2)=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22596384N-(5-chloropyridin-2-yl)-2-(4-cyanobenzamido)-5-methoxybenzamide

Product 1

HCID 22596367N-(5-chloro(2-pyridyl)){6-[(4-cyanophenyl)-carbonylamino]3-hydroxyphenyl}carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of compound N-(5-chloro(2-pyridyl)){2-[(4-cyanophenyl)-carbonylamino]-5-methoxyphenyl}carboxamide (500 mg, 1.2 mmol) in DCM (100 mL) at −78° C. was added BBr3 (2 mL). The mixture was stirred at ambient temperatures for 72 hours. The solid was collected by filtration and was washed by DCM and water, dried under vacuum. The filtrate was concentrated and extracted with EtOAc. The organic extract was washed with brine, dried and evaporated. The resulting solid was combined with the solid obtained from filtration to give the title compound. Total yield is 90% (430 mg). MS found for C20H13ClN4O3 (M+H)+: 393.0.

Workup

  1. filtrationThe solid was collected by filtration
  2. washwas washed by DCM and water
  3. customdried under vacuum
  4. concentrationThe filtrate was concentrated
  5. extractionextracted with EtOAc
  6. extractionThe organic extract
  7. washwas washed with brine
  8. customdried
  9. customevaporated
  10. customobtained from filtration

Sources & evidence

ORD record
ord-459c7bb1e1b64d9fb235c56883919cac
Source dataset
uspto-grants-2015_08
Patent number
US09108922B2

Reaction notes

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