Cesium carbonate → 2-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridine

HRID 2196442Notes

Reaction equation

HRID 2196442 reaction equation
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][O:5][Si:6]([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[Cl:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][C:23](B3OC(C)(C)C(C)(C)O3)=[CH:22][N:21]2[CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.O>[Si:6]([O:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[C:35]1[N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19][C:18]=1[Cl:17])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 13424900(2-Bromobenzyloxy)tert-butyldimethylsilaneHCID 442323732-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine

Product 1

HCID 866520702-[(tert-Butyldimethylsilanyl)oxymethyl]phenyl-2-chloroimidazo[1,2-a]pyridineYield 46.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

450 mg of (2-bromobenzyloxy)-tert-butyldimethylsilane, 500 mg of 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)imidazo[1,2-a]pyridine and 1.46 g of caesium carbonate are dissolved in 8 ml of tetrahydrofuran and 1 ml of water. The mixture is degassed with argon for 10 min, 110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added and the mixture is heated at the reflux of the solvent for 16 hours. After cooling, the reaction mixture is hydrolysed with water, and the organic phase, which has been extracted with dichloromethane, is separated, dried and concentrated under reduced pressure. The oil obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 260 mg of compound are obtained.

Workup

  1. customThe mixture is degassed with argon for 10 min
  2. addition110 mg of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium are added
  3. temperaturethe mixture is heated at the
  4. temperaturereflux of the solvent for 16 hours
  5. temperatureAfter cooling
  6. extractionthe organic phase, which has been extracted with dichloromethane
  7. customis separated
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe oil obtained
  11. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-d9717c96f6fc459b91c5f9e7127a7d55
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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