Acetonitrile → HCID 23649449, compound

HRID 600621Notes

Reaction equation

HRID 600621 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[N:10]=2)[CH:7]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>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.C1(C)C=CC=CC=1>[C:13]1([C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:7][N:6]3[CH:8]=2)=[O:12])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 67273324HCID 67273324, compound

Product 1

HCID 23649449HCID 23649449, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

0.391 g of (6-bromoimidazo[1,2-a]pyridin-2-yl)(phenyl)methanone, 0.237 g of phenylboronic acid, 45 mg of tetrakis(triphenylphosphine)palladium, 4 mL of aqueous 2M sodium carbonate solution, 6 mL of acetonitrile and 6 mL of toluene are introduced into a 20 mL microwave tube. The mixture is stirred for 20 minutes in a microwave machine set at 150° C. After cooling, the organic phase is separated out, dried and evaporated. The residue is taken up in a mixture of dichloromethane and pentane. The solid is filtered off and then purified by trituration in methanol to give 0.16 g of phenyl(6-phenylimidazo[1,2-a]pyridin-2-yl)methanone in the form of an off-white solid.

Workup

  1. customset at 150° C
  2. temperatureAfter cooling
  3. customthe organic phase is separated out
  4. customdried
  5. customevaporated
  6. additionThe residue is taken up in a mixture of dichloromethane and pentane
  7. filtrationThe solid is filtered off
  8. custompurified by trituration in methanol

Sources & evidence

ORD record
ord-b9094053be7949b3b0eb218040975a36
Source dataset
uspto-grants-2011_03
Patent number
US07902219B2

Reaction notes

Loading…