Phthalic Anhydride → 3-[N-(2-carboxybenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

HRID 1886456Notes

Reaction equation

HRID 1886456 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[C:26]1(=[O:36])[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12>CN(C=O)C>[C:29]([C:28]1[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=1[C:26]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([CH3:21])=[CH:18][C:19]([CH3:20])=[C:14]4[N:13]=[C:12]3[CH2:22][CH3:23])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)=[O:36])([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 24758Sodium hydrideHCID 100407273-(5-indolyl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 100268683-[N-(2-carboxybenzoyl)-5-indolyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of Step A (75 mg, 0.25 mmol) in 3 mL of DMF was added 11 mg (0.27 mmol, 1.1 eq) of 60% NaH, followed by 45 mg (0.30 mmol, 1.2 eq) of phthalic anhydride. This mixture was stirred for 16 hours and the DMF removed in vacuo. The resultant oil was flash column chromatographed with 15% of (10/1) mixture of methanol/NH4OH in CHCl3 to yield the titled compound (53 mg, 47%).

Workup

  1. customthe DMF removed in vacuo
  2. customchromatographed with 15% of (10/1) mixture of methanol/NH4OH in CHCl3

Sources & evidence

ORD record
ord-802584dede6348459bae1151ee9896a0
Source dataset
uspto-grants-1992_09
Patent number
US05151435

Reaction notes

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