2-Chloronicotinoyl chloride → N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamide

HRID 2380237Notes

Reaction equation

HRID 2380237 reaction equation
[NH2:1][C:2]1[C:3]([Br:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[Cl:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>C(Cl)Cl.N1C=CC=CC=1>[Br:10][C:3]1[C:2]([NH:1][C:14]([C:13]2[C:12]([Cl:11])=[N:20][CH:19]=[CH:18][CH:17]=2)=[O:15])=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[N:4]=1

Participants

5

Reactant 2

HCID 27745412-Chloronicotinoyl chlorideHCID 152093242-Bromo-6-methoxypyridin-3-amine

Product 1

HCID 10617311N-(2-Bromo-6-methoxy-3-pyridinyl)-2-chloro-3-pyridinecarboxamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-amino-2-bromo-6-methoxypyridine (2.7 g) in methylene chloride (20 ml) and pyridine (1 ml) was added 2-chloronicotinoyl chloride (2.2 g), and the resulting mixture was stirred 20 min. The mixture was then diluted with methylene chloride (100 ml), washed with water (100 ml), dried (anhydrous magnesium sulfate), and concentrated. The semisolid residue was saturated with hexane, filtered, and dried to give 4.1 g of product suitable for use in the next reaction.

Workup

  1. washwashed with water (100 ml)
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-0adc9dccc4984cb0a0bf3a9877ae43bf
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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