Acetonitrile → [3-(2-(Benzofuran-3-yl)imidazo[1,2-a]pyridin-6-yl)phenyl]methanol

HRID 2196450Notes

Reaction equation

HRID 2196450 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15](Br)=[CH:14][N:13]3[CH:19]=2)=[CH:2]1.[OH:20][CH2:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][CH:27]=1.C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>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>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[N:11]=[C:12]3[CH:17]=[CH:16][C:15]([C:26]4[CH:27]=[C:22]([CH2:21][OH:20])[CH:23]=[CH:24][CH:25]=4)=[CH:14][N:13]3[CH:19]=2)=[CH:2]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 686400892-(Benzofuran-3-yl)-6-bromoimidazo[1,2-a]pyridine

Product 1

HCID 68639346[3-(2-(Benzofuran-3-yl)imidazo[1,2-a]pyridin-6-yl)phenyl]methanolYield 40.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

100 mg of 2-(benzofuran-3-yl)-6-bromoimidazo[1,2-a]pyridine, 73 mg of 3-(hydroxymethyl)phenylboronic acid and 11 mg of tetrakis(triphenylphosphine)palladium are placed in a microwave tube. 2 ml of acetonitrile, 2 ml of toluene and 1.5 ml of a 2M solution of sodium carbonate are added thereto. The tube is placed in a microwave device and irradiated at 150° C. for 15 min. The organic phase is separated, dried, and then concentrated under reduced pressure. The oily residue is taken up with 3 ml of dichloromethane and triturated for 1 hour. The precipitate is recovered by filtration, washed with diisopropyl ether and dried in a desiccator under reduced pressure. 44 mg of compound are obtained.

Workup

  1. customirradiated at 150° C. for 15 min
  2. customThe organic phase is separated
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customtriturated for 1 hour
  6. filtrationThe precipitate is recovered by filtration
  7. washwashed with diisopropyl ether
  8. customdried in a desiccator under reduced pressure

Sources & evidence

ORD record
ord-b75160df44a144d4bb3017dd0491e04f
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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