6-Bromo-2-phenylimidazo[1,2-a]pyridine → [4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol

HRID 606005Notes

Reaction equation

HRID 606005 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][CH:14]=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[OH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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.C(#N)C>[C:11]1([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([C:22]4[CH:23]=[CH:24][C:19]([CH2:18][OH:17])=[CH:20][CH:21]=4)=[CH:7][N:6]3[CH:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 6234306-Bromo-2-phenylimidazo[1,2-a]pyridineHCID 27347064-(Hydroxymethyl)benzeneboronic acid

Product 1

HCID 24855995[4-(2-Phenylimidazo[1,2-a]pyridin-6-yl)phenyl]methanolYield 31.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

150 mg of 6-bromo-2-phenylimidazo[1,2-a]pyridine, 125 mg of 4-(hydroxymethyl)phenylboronic acid, 19 mg of tetrakis(triphenylphosphine)palladium and 2 ml of acetonitrile are placed in a microwave tube. Under a stream of nitrogen, 2 ml of nitrogen-degassed toluene and then 2 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 recovered, dried and then concentrated under reduced pressure. The residue is taken up with diisopropyl ether and the precipitate is recovered by filtration, washed and dried. It is purified by recrystallization from n-butanol. 52 mg of compound are obtained. Mp=238-240° C. 1H NMR (DMSO-d6, δ in ppm): 4.54 (d, J=5.5 Hz, 2H); 5.2 (t, J=5.6 Hz, 1H); from 7.24 to 7.73 (m, 9H); 7.96 (m, 2H); 8.36 (s, 1H); 8.84 (t, J=1.3 Hz, 1H). M+H=301.

Workup

  1. customUnder a stream of nitrogen, 2 ml of nitrogen-degassed toluene
  2. addition2 ml of a 2M solution of sodium carbonate are added
  3. customirradiated at 150° C. for 15 min
  4. customThe organic phase is recovered
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. filtrationthe precipitate is recovered by filtration
  8. washwashed
  9. customdried
  10. customIt is purified by recrystallization from n-butanol

Sources & evidence

ORD record
ord-f7701a5c209f4245be042274300ca1a1
Source dataset
uspto-grants-2011_03
Patent number
US07915284B2

Reaction notes

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