Acetonitrile → {2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanol

HRID 606014Notes

Reaction equation

HRID 606014 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.[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(#N)C.C(=O)([O-])O.[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>[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:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[CH2:19][OH:18])=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 516892Sodium BicarbonateHCID 8282916-Bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridineHCID 43742622-(Hydroxymethyl)phenylboronic Acid

Product 1

HCID 67046191{2-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]phenyl}methanolYield 58.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under a stream of nitrogen, 200 mg of 6-bromo-2-(4-chlorophenyl)imidazo[1,2-a]pyridine (prepared as described in 5.1), 148 mg of 2-(hydroxymethyl)phenyl boronic acid and 22.5 mg of tetrakis(triphenylphosphine)palladium are placed in a microwave tube containing a mixture of 3 ml of acetonitrile, 3 ml of toluene and 3 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. The residue is purified by silica gel chromatography, elution being carried out with a 98/2 dichloromethane/methanol mixture. The solid obtained is triturated in diisopropyl ether and recovered by filtration and then dried in a dessicator under reduced pressure. 127 mg of compound are obtained. Mp=164-166° C. 1H NMR (DMSO-d6, δ in ppm): 4.44 (d, J=5.6 Hz, 2H); 5.19 (t, J=5.4 Hz, 1H); from 7.25 to 7.64 (m, 8H); 7.98 (m, J=8.3 Hz, 2H); 8.41 (s, 1H); 8.54 (m, 1H). M+H=335.

Workup

  1. additioncontaining
  2. customirradiated at 150° C. for 15 min
  3. customThe organic phase is separated
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by silica gel chromatography, elution
  7. customThe solid obtained
  8. customis triturated in diisopropyl ether
  9. filtrationrecovered by filtration
  10. customdried in a dessicator under reduced pressure

Sources & evidence

ORD record
ord-1b80f4de4d1a44f6832ab4fe848713cf
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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