Water → 5-Bromo-n-(2,6-dichloro-4-methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide

HRID 2229321Notes

Reaction equation

HRID 2229321 reaction equation
CC([O-])=O.[K+].[Cl:6][C:7]1[C:12]([NH:13][C:14]([C:16]2[C:17]([NH:22][CH2:23][CH3:24])=[N:18][CH:19]=[CH:20][CH:21]=2)=[O:15])=[C:11]([CH3:25])[CH:10]=[C:9]([Cl:26])[N:8]=1.[Br:27]Br.O>CC(O)=O>[Br:27][C:20]1[CH:21]=[C:16]([C:14]([NH:13][C:12]2[C:7]([Cl:6])=[N:8][C:9]([Cl:26])=[CH:10][C:11]=2[CH3:25])=[O:15])[C:17]([NH:22][CH2:23][CH3:24])=[N:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24408Bromine3×HCID 517044Potassium Acetate3×HCID 10782273n-(2,6-Dichloro-4methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide

Product 1

HCID 184666225-Bromo-n-(2,6-dichloro-4-methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Solid KOAc (22.2 g, 229 mmol) was added to a solution of crude N-(2,6-dichloro-4methyl-3-pyridinyl)-2-(ethylamino)-3-pyridinecarboxamide (61.98 g, <190 mmol) in AcOH (600 mL). A solution of Br2 (9.7 mL, 191 mmol) was then added over 30 min. After stirring 30 min, additional amounts of KOAc and Br2 were introduced until TLC indicated that no starting material remained (a total of 11.2 g of KOAc and 5.91 mL of Br2). The solution was then poured into water (2 L) and stirred for 20 min. The solid was removed by filtration and then dissolved in Et2O (1 L). The ethereal solution was washed with water (3×), aqueous saturated NaHCO3, brine then dried (MgSO4) to give a mixture containing, as the major component, the title compound (77.7 g, yellow foam). The material was used directly in the subsequent reaction.

Workup

  1. stirringstirred for 20 min
  2. customThe solid was removed by filtration
  3. dissolutiondissolved in Et2O (1 L)
  4. washThe ethereal solution was washed with water (3×), aqueous saturated NaHCO3, brine
  5. dry with materialthen dried (MgSO4)
  6. customto give a mixture
  7. additioncontaining, as the major component

Sources & evidence

ORD record
ord-b47e618e7ca24f2ab1cdcf597df120fe
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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