Water → HCID 18466625, compound

HRID 2229306Notes

Reaction equation

HRID 2229306 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](Cl)=[O:10])[C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:12][C:13]1[C:14]([NH:20][CH2:21][CH3:22])=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=1.C([O-])(O)=O.[Na+].O>CC#N>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([NH:12][C:13]2[C:14]([NH:20][CH2:21][CH3:22])=[N:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:10])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 10797271HCID 10797271, compoundHCID 126772955-Bromo-2-chloro-3-pyridinecarbonyl chloride

Product 1

HCID 18466625HCID 18466625, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 5-bromo-2-chloro-3-pyridinecarbonyl chloride (30.0 g, 97.0 mmol) in MeCN (100 mL) was added via cannula to a solution of 3-amino-6-chloro-2-(ethylamino)pyridine (16.6 g, 97.0 mmol) in MeCN (180 mL) containing solid NaHCO3 (14.2 g, 169 mmol) at room temperature. The mixture was stirred at room temperature for 1 h. Water (200 mL) was added and the mixture was stirred for 10 min. The resulting suspension was filtered. The solid was washed with Et2O (50 mL) and concentrated from pyridine solution (3×50 mL) to give the title compound (28.4 g, 75% yield).

Workup

  1. stirringthe mixture was stirred for 10 min
  2. filtrationThe resulting suspension was filtered
  3. washThe solid was washed with Et2O (50 mL)
  4. concentrationconcentrated from pyridine solution (3×50 mL)

Sources & evidence

ORD record
ord-1f98b504cb8a4793ab3cab7d384dd18a
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

Loading…