Toluene → 1-{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanone

HRID 606013Notes

Reaction equation

HRID 606013 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[C:18](#N)[CH3:19].C(=O)([O-])[OH:22].[Na+].[C:26]1(C)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:27]4[CH:28]=[C:29]([C:18](=[O:22])[CH3:19])[CH:30]=[CH:31][CH:26]=4)=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 8282916-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine

Product 1

HCID 670470901-{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}ethanone

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

300 mg of 6-bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine (prepared as described in 5.1), 240 mg of 3-acetylboronic acid and 34 mg of tetrakis(triphenylphosphine)palladium are mixed in a microwave tube containing 4.5 ml of acetonitrile, 4.5 ml of toluene and 4.5 ml of a 2M solution of sodium hydrogen carbonate. The tube is placed in a microwave apparatus and irradiated at 150° C. for 15 min. The organic phase is separated, dried and concentrated under reduced pressure. A solid residue is obtained which is triturated in a mixture of 3 ml of dichloromethane and 3 ml of diisopropyl ether for 30 min. The precipitate is recovered by filtration, washed with diisopropyl ether and dried in a desiccator under reduced pressure. 209 mg of compound are obtained. Mp=173-175° C.

Workup

  1. customirradiated at 150° C. for 15 min
  2. customThe organic phase is separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customA solid residue is obtained which
  6. customis triturated in a mixture of 3 ml of dichloromethane and 3 ml of diisopropyl ether for 30 min
  7. filtrationThe precipitate is recovered by filtration
  8. washwashed with diisopropyl ether
  9. customdried in a desiccator under reduced pressure

Sources & evidence

ORD record
ord-f3a61aa8e787406f82efeea532d8fbce
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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