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

HRID 558102Notes

Reaction equation

HRID 558102 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-6b60845b581640b18cdfae9faf26a4a9
Source dataset
uspto-grants-2011_11
Patent number
US08063036B2

Reaction notes

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