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Water → 2-Chloro-N-{2-(ethylarnino)-6-fluoro-3pyridinyl}-5-bromo-3-pyridinecarboxamide

HRID 2229315
Notes
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Reaction equation

HRID 2229315 reaction equation
[NH2:1][C:2]1[C:3]([NH:9][CH2:10][CH3:11])=[N:4][C:5]([F:8])=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].[Br:17][C:18]1[CH:19]=[C:20]([C:25](Cl)=[O:26])[C:21]([Cl:24])=[N:22][CH:23]=1.O>CC#N>[Cl:24][C:21]1[C:20]([C:25]([NH:1][C:2]2[C:3]([NH:9][CH2:10][CH3:11])=[N:4][C:5]([F:8])=[CH:6][CH:7]=2)=[O:26])=[CH:19][C:18]([Br:17])=[CH:23][N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chlorideHCID 184666123-Amino-2-(ethylamino)-6-fluoropyridine

Product 1

HCID 184666372-Chloro-N-{2-(ethylarnino)-6-fluoro-3pyridinyl}-5-bromo-3-pyridinecarboxamideYield 99%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Procedure

To a cooled solution (4° C.) of 3-amino-2-(ethylamino)-6-fluoropyridine (31.0 g, 200 mmol) in MeCN (160 mL) was added solid NaHCO3 (50.4 g, 600 mmol). After 15 min, a solution of 5-bromo-2-chloro-3-pyridinecarbonyl chloride (1 equiv., 200 mmol) in MeCN (155 mL) was added. After 60 min at room temperature, the reaction mixture was poured into water (1.2 L) and stirred for 30 min. The resulting solid was filtered, dried under reduced pressure at 50° C. overnight. The title compound (73.7 g, 99% yield) was obtained as a black solid.

Workup

  1. waitAfter 60 min at room temperature
  2. filtrationThe resulting solid was filtered
  3. customdried under reduced pressure at 50° C. overnight

Sources & evidence

ORD record
ord-507b7af3e4344117b8a83c90dde5c542
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06420359B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes