2-Chloro-5-nitrobenzoic acid → HCID 90450868, compound

HRID 589803Notes

Reaction equation

HRID 589803 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:12]=1[C:13](O)=O>>[Br:1][C:2]1[CH:3]=[C:4]2[NH:9][C:13]([C:12]3[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:11]=3[Cl:10])=[N:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 90450868HCID 90450868, compoundYield 127.6%

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromopyridine-2,3-diamine (15 g, 79.78 mmol, 1.00 equiv), 2-chloro-5-nitrobenzoic acid (17.7 g, 87.81 mmol, 1.10 equiv) in PPA (200 mL) was stirred overnight at 130° C. and then quenched by the addition of 300 mL of H2O/ice. The pH value of the mixture was adjusted to 8 with sodium carbonate and the solids were collected by filtration, washed with water and dried in an oven under reduced pressure to give 36 g (crude) of 6-bromo-2-(2-chloro-5-nitrophenyl)-1H-imidazo[4,5-b]pyridine I-2a as a brown solid.

Workup

  1. customquenched by the addition of 300 mL of H2O/ice
  2. filtrationthe solids were collected by filtration
  3. washwashed with water
  4. customdried in an oven under reduced pressure

Sources & evidence

ORD record
ord-316293e0069a49fcbbfa605c53d9eafc
Source dataset
uspto-grants-2016_01
Patent number
US09233961B2

Reaction notes

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