Cesium carbonate → HCID 67323824, compound

HRID 1616930Notes

Reaction equation

HRID 1616930 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[CH:28]=[N:29][CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1.[CH:37]([Si:40]([CH:45]([CH3:47])[CH3:46])([CH:42]([CH3:44])[CH3:43])[SH:41])([CH3:39])[CH3:38]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:34][C:33]([F:36])([F:35])[C:31]1[CH:30]=[N:29][CH:28]=[C:27]([S:41][Si:40]([CH:42]([CH3:44])[CH3:43])([CH:45]([CH3:47])[CH3:46])[CH:37]([CH3:38])[CH3:39])[CH:32]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 3435097Tris(propan-2-yl)silanethiolHCID 111279913-Bromo-5-(trifluoromethyl)pyridine

Product 1

HCID 67323824HCID 67323824, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Anhydrous toluene was bubbled with Argon for 1 h before being used. Palladium acetate (0.050 g, 0.22 mmol), triphenylphosphine (0.255 g, 0.973 mmol), cesium carbonate (1.87 g, 5.75 mmol) and 3-bromo-5-trifluoromethyl-pyridine (1.00 g, 4.42 mmol) were introduced into a 50 mL round bottom flask under argon. Toluene (10 mL) and triisopropylsilanethiol (1.23 mL, 5.75 mmol) were added. The reaction was stirred at 100° C. overnight, then cooled to room temperature and diluted with hexanes. The suspension was filtered through a plug of Celite. The filtrate was concentrated down to afford 3-trifluoromethyl-5-triisopropylsilanylsulfanyl-pyridine which was used in the next reaction step without further purification.

Workup

  1. customAnhydrous toluene was bubbled with Argon for 1 h
  2. temperaturecooled to room temperature
  3. filtrationThe suspension was filtered through a plug of Celite
  4. concentrationThe filtrate was concentrated down

Sources & evidence

ORD record
ord-561f1999fa93482599f7ec3132de1870
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…