Phosphorus oxybromide → 3-bromo-6-(4-methylsulfonylphenyl)-N-phenyl-pyrazine-2-carboxamide

HRID 522527

Reaction equation

HRID 522527 reaction equation
O[C:2]1[C:3]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.P(Br)(Br)([Br:29])=O.C(=O)(O)[O-].[Na+].C(Cl)Cl>C1(C)C=CC=CC=1>[Br:29][C:2]1[C:3]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 23716255Sodium bicarbonate methylene chlorideHCID 1785046823-hydroxy-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide

Product 1

HCID 866651473-bromo-6-(4-methylsulfonylphenyl)-N-phenyl-pyrazine-2-carboxamideYield 120.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-hydroxy-6-(4-(methylsulfonyl)phenyl)-N-phenylpyrazine-2-carboxamide (84.3 mg, 0.1712 mmol) in toluene (3.000 mL) was treated with POBr3 (196.3 mg, 0.6848 mmol) and the resultant mixture was heated to 100° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and treated with sodium bicarbonate/DCM. The organic layer was separated, dried (Na2SO4), filtered and concentrated in vacuo to give the impure desired product as a yellow solid (89.4 mg, 95% Yield). MS (ES+) 433.88.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06889cf9843647b28406c1fe6d6326d2
Source dataset
uspto-grants-2016_05
Patent number
US09334244B2

Linked notes

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