Tributylstannane → (1,1-Dimethylethyl)(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)dimethylsilane

HRID 1662490Notes

Reaction equation

HRID 1662490 reaction equation
Cl[CH:2]([C:7]1[CH:12]=[C:11]([CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH:10]=[CH:9][C:8]=1[C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[F:30])[C:3]([CH3:6])([CH3:5])[CH3:4].CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:21][C:18]([Si:15]([O:14][CH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[F:30])=[C:7]([CH2:2][C:3]([CH3:6])([CH3:5])[CH3:4])[CH:12]=1)([CH3:16])[CH3:17])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 57706174HCID 57706174, compound

Product 1

HCID 57706342(1,1-Dimethylethyl)(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-yl)methyl)oxy)dimethylsilaneYield 94.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 69.16B (0.015 g, 0.033 mmol) in toluene (2.00 mL) at 23° C. was added AIBN (0.00055 g, 0.0033 mmol) followed by tri-n-butyltin hydride (0.048 g, 0.17 mmol). The reaction was stirred at 100° C. for two hours. After which, the reaction was cooled to room temperature and concentrated in vacuo. The product was then purified on silica gel (0-10% EtOAc in hexanes) to yield 69.16D as a colorless oil (0.013 g, 94% yield).

Workup

  1. temperatureAfter which, the reaction was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe product was then purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-12689a3627a04cbeb035459f081d0953
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…