Ethanol → 3-[3-bromo-2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

HRID 274143Notes

Reaction equation

HRID 274143 reaction equation
C(O)C.[OH-].[Na+].[Br:6][C:7]1[N:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([O:38]CC)=[O:37])[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][N:17]1[C:21]3=[N:22][CH:23]=[CH:24][C:25]([CH3:26])=[C:20]3[N:19]=[C:18]1[CH2:27][CH2:28][CH3:29])[CH:12]=[CH:11]2>O>[Br:6][C:7]1[N:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:36]([OH:38])=[O:37])[N:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][N:17]1[C:21]3=[N:22][CH:23]=[CH:24][C:25]([CH3:26])=[C:20]3[N:19]=[C:18]1[CH2:27][CH2:28][CH3:29])[CH:12]=[CH:11]2

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 200945323-[3-bromo-2-(2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 200945473-[3-bromo-2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridineYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethanol (1.2 ml), water (0.3 ml), and sodium hydroxide (34 mg, 0.840 mmol) were added to 3-[3-bromo-2-(2-ethoxycarbonylphenyl)-2H-indazol-5-yl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine (0.149 mg, 0.280 mmol) obtained from two batches of Example 19, and the mixture was stirred at room temperature for 15.5 hours. After concentration, it was partitioned by water (2.5 ml) and ether (5 ml). Conc. hydrochloric acid was dropwise added to the water layer while stirring so as to adjust its pH to 5. The resultant solid was filtered off, washed twice with water (1 ml), and dried overnight at 37° C. to give 84 mg of 3-[3-bromo-2-(2-carboxyphenyl)-2H-indazol-5-yl]methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine.

Workup

  1. customobtained from two batches of Example 19
  2. concentrationAfter concentration, it
  3. customwas partitioned by water (2.5 ml) and ether (5 ml)
  4. additionConc. hydrochloric acid was dropwise added to the water layer
  5. stirringwhile stirring so as
  6. filtrationThe resultant solid was filtered off
  7. washwashed twice with water (1 ml)
  8. customdried overnight at 37° C.

Sources & evidence

ORD record
ord-0240e644c1234a82a605cf52d11fc2f5
Source dataset
uspto-grants-1995_02
Patent number
US05387684

Reaction notes

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