Potassium Carbonate → methyl 3-(4-acetoxy-2-chlorobenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate

HRID 2181024Notes

Reaction equation

HRID 2181024 reaction equation
[CH3:1][C:2]1[NH:15][C:5]2=[N:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][C:9]([CH3:10])=[C:4]2[N:3]=1.[C:16]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[C:22]([Cl:28])[CH:21]=1)(=[O:18])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:16]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:15]2[C:5]3=[N:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][C:9]([CH3:10])=[C:4]3[N:3]=[C:2]2[CH3:1])=[C:22]([Cl:28])[CH:21]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 223879114-Acetoxy-2-chlorobenzylbromideHCID 22388027methyl 2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate

Product 1

HCID 22485009methyl 3-(4-acetoxy-2-chlorobenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylateYield 117.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (2.70 g), 4-acetoxy-2-chlorobenzylbromide (4.85 g), potassium carbonate (2.73 g) and N,N-dimethylformamide (27 ml) was stirred at room temperature for 5 hr and left standing overnight. The reaction mixture was partitioned between ethyl acetate and saturated brine, and the resulting precipitate was collected by filtration and washed with water and ethyl acetate to give methyl 3-(4-acetoxy-2-chlorobenzyl)-2,7-dimethyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (6.0 g) as a pale-brown powder. The mother liquor and washing were combined and the organic layer was separated, dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was powdered from diethyl ether to give the second lot (680 mg) as a pale-brown powder.

Workup

  1. waitleft
  2. waitstanding overnight
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated brine
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water and ethyl acetate

Sources & evidence

ORD record
ord-1ea31318b7fe4523a7c94167c2ed69b4
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Reaction notes

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