2-Chloroaniline → 2-(4-Bromophenyl)-N-(2-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamide

HRID 2073019Notes

Reaction equation

HRID 2073019 reaction equation
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:22]([CH2:23][C:24]([OH:26])=O)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:10][CH:9]=1.[Cl:27][C:28]1[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=1[NH2:30].C(N(CC)CC)C>CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:22]([CH2:23][C:24]([NH:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[Cl:27])=[O:26])[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[N:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 72402-ChloroanilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 143904564-bromophenyl-3H-imidazo[4,5-b]pyridine-3-acetic acid

Product 1

HCID 143902992-(4-Bromophenyl)-N-(2-chlorophenyl)-3H-imidazo[4,5-b]pyridine-3-acetamideYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere, oxalyl chloride (3.2 g, 0.025 mole) was added dropwise (slowly) to a stirred and chilled (5°-10° C.) solution of 2-(4-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid (8.0 g, 0.024 mole) in anhydrous dimethylformamide (50 ml). The reaction mixture was heated at 55°-60° C. for 4 hrs, cooled to room temperature, and added dropwise to a stirred and chilled (10°-15° C.) solution of 2-chloroaniline (3.2 g, 0.25 mole) and triethylamine (2.5 g, 0.025 mole) in anhydrous dimethylformamide (100 ml). The reaction mixture was stirred at room temperature overnight, filtered, and poured into water (350 ml). The mixture was allowed to precipitate and filtered. The filter cake was twice suspended in water (250 ml) and filtered. The filter cake was air dried and twice recrystallized from tetrahydrofuran to give 4.22 g (40%) of a white solid, mp. 230.5°-232° C.

Workup

  1. temperatureThe reaction mixture was heated at 55°-60° C. for 4 hrs
  2. additionadded dropwise to
  3. stirringa stirred
  4. stirringThe reaction mixture was stirred at room temperature overnight
  5. filtrationfiltered
  6. additionpoured into water (350 ml)
  7. customto precipitate
  8. filtrationfiltered
  9. filtrationfiltered
  10. customdried
  11. customtwice recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-33277df9ac6a4c268abe63f1cdface03
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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