Sodium Hydroxide → 7-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 1766792Notes

Reaction equation

HRID 1766792 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[C:8]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[C:9]([Cl:16])[C:10]2[N:11]([CH:13]=[CH:14][N:15]=2)[CH:12]=1)=[O:6]>CO>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:8]2[C:7]([C:5]([OH:6])=[O:4])=[CH:12][N:11]3[CH:13]=[CH:14][N:15]=[C:10]3[C:9]=2[Cl:16])=[C:19]([Cl:25])[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58886653Methyl 7-(4-bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 115964897-(4-Bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium hydroxide (1.0 M aqueous solution, 14.6 mL, 14.6 mmol) was added to a solution of 7-(4-bromo-2-chlorophenylamino)-8-chloroimidazo[1,2-a]pyridine-6-carboxylic acid methyl ester (29) in methanol (30 mL) and the solution allowed to stir at room temperature overnight. Methanol was removed by rotary evaporation and the solution diluted with water and acidified to pH 2 by addition of 1.0 M HCl. The aqueous suspension was extracted with 4:1 ethyl acetate/THF. The organic extracts were washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to provide the desired product as a light orange solid (30). MS (APCI+) m/z 400, 402, 404 (M+: Cl, Br pattern) detected. 1H NMR (400 MHz, methanol-d4) δ 9.01 (s, 1H), 7.83 (s, 1H), 7.51 (s, 2H), 7.25 (d, 1H), 6.60 (d, 1H).

Workup

  1. customMethanol was removed by rotary evaporation
  2. additionthe solution diluted with water
  3. additionacidified to pH 2 by addition of 1.0 M HCl
  4. extractionThe aqueous suspension was extracted with 4:1 ethyl acetate/THF
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over NaSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-49856dc55af5461f92838e009b413e7d
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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