Water → 3-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

HRID 383303Notes

Reaction equation

HRID 383303 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH3:11][NH:12][C:13]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)=[O:14].O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:10]1[CH:9]=[CH:8][N:5]2[CH:6]=[CH:7][C:2]([C:19]3[CH:20]=[C:15]([CH:16]=[CH:17][CH:18]=3)[C:13]([NH:12][CH3:11])=[O:14])=[CH:3][C:4]=12

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27735243-(Methylcarbamoyl)benzeneboronic acidHCID 150989037-Bromoimidazo(1,2-a)pyridine

Product 1

HCID 684844493-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

7-Bromo-imidazo-[1,2-a]-pyridine (1 eq, 0.5 mmol, 100 mg) and (3-methylamino carbonylphenyl)boronic acid (1.1 eq, 0.558 mmol, 99.9 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 1.52 mmol, 161 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.025 mmol, 17.8 mg) is then added and the reaction mixture is heated using microwave radiation at 120° C. for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 3-imidazo[1,2-a]pyridine-7-yl-N-methyl-benzamide as a brown solid; [M+H]+=252

Workup

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 10 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

Sources & evidence

ORD record
ord-b91d90e9ac9f49029ba0eea0655cce7b
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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