Triethylsilane → HCID 66839133, compound

HRID 546784Notes

Reaction equation

HRID 546784 reaction equation
C([SiH](CC)CC)C.FC(F)(F)S(O[C:14]1[C:19]([N:20]2[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]2)=[CH:18][CH:17]=[C:16](/[CH:26]=[CH:27]/[C:28]2[N:46]=[C:31]3[CH:32]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=4[C:42]([F:45])([F:44])[F:43])[CH2:33][CH2:34][CH2:35][N:30]3[N:29]=2)[N:15]=1)(=O)=O>CN(C=O)C>[CH3:25][C:23]1[N:22]=[CH:21][N:20]([C:19]2[CH:18]=[CH:17][C:16](/[CH:26]=[CH:27]/[C:28]3[N:46]=[C:31]4[CH:32]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=5[C:42]([F:44])([F:45])[F:43])[CH2:33][CH2:34][CH2:35][N:30]4[N:29]=3)=[N:15][CH:14]=2)[CH:24]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 86628518HCID 86628518, compound

Product 1

HCID 66839133HCID 66839133, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Triethylsilane (40.9 μL) and a 1,1′-bis(diphenylphosphino)ferrocene palladium (II) dichloride-dichloromethane complex (4.37 mg) were added to a solution of 3-(4-methyl-1H-imidazol-1-yl)-6-{(E)-2-[8-(2-trifluoromethylphenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-yl]vinyl}pyridin-2-yl trifluoromethanesulfonate (64 mg) in DMF (2 mL). The reaction solution was stirred at 70° C. for five hours. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=4:1→ethyl acetate) to obtain a racemate of the title compound (25 mg). The resulting racemate (25 mg) was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: ethanol, flow rate: 11 mL/min) to obtain the title optically active compound with a retention time of 21 minutes and positive optical rotation (10 mg) and the title optically active compound with a retention time of 30 minutes and negative optical rotation (10 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (carrier: Chromatorex NH; elution solvent: heptane:ethyl acetate=4:1→ethyl acetate)

Sources & evidence

ORD record
ord-d4a66a1c715c43aca60d6a0399954702
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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