Thionyl Chloride → 5-Bromo-2-chloro-N-[2-(ethylamino)pyridin-3-yl]pyridine-3-carboxamide

HRID 2229302Notes

Reaction equation

HRID 2229302 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])(O)=O.[Na+].[Br:16][C:17]1[CH:18]=[C:19]([C:24](Cl)=[O:25])[C:20]([Cl:23])=[N:21][CH:22]=1.BrC1C=C(C(O)=O)C(O)=NC=1.O=S(Cl)Cl>CC#N>[Cl:23][C:20]1[C:19]([C:24]([NH:1][C:2]2[C:3]([NH:8][CH2:9][CH3:10])=[N:4][CH:5]=[CH:6][CH:7]=2)=[O:25])=[CH:18][C:17]([Br:16])=[CH:22][N:21]=1

Participants

7

Reactant 5

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chlorideHCID 13451717N~2~-Ethylpyridine-2,3-diamineHCID 178418525HCID 178418525, compound

Product 1

HCID 120157285-Bromo-2-chloro-N-[2-(ethylamino)pyridin-3-yl]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a cooled solution of 3-amino-2-(ethylamino)pyridine (30.6 g, 223 mmol) in MeCN (740 mL) was added solid NaHCO3 (56.3 g, 669 mmol). After 5 min, crude 5-bromo-2-chloro-3-pyridinecarbonyl chloride (prepared from 5-bromo-2-hydroxy-3-pyridinecarboxylic acid and SOCl2 [as described by T. W. Gero et al. in Synth. Commun. 1989, 19, 553-559 (incorporated herein by reference) but with omission of the aqueous work-up] was added (1 equiv., 223 mmol). After 2 h, the reaction mixture was poured over ice/H2O (1.5 L) and the resulting solid was filtered, rinsed with H2O and then hexane. After drying under reduced pressure overnight, the title compound was obtained as a black solid (54.9 g, 69% yield).

Workup

  1. additionwas added (1 equiv., 223 mmol)
  2. waitAfter 2 h
  3. filtrationthe resulting solid was filtered
  4. washrinsed with H2O
  5. customAfter drying under reduced pressure overnight

Sources & evidence

ORD record
ord-9c9d9fc506094016bc60f1b2de21d174
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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