Toluene → HCID 137328926, compound

HRID 1296003Notes

Reaction equation

HRID 1296003 reaction equation
[C:1]([C:5]1([SiH2:11][C:12]([O:27][C:28]([C:47]2[CH:48]=[N:49][C:50](Cl)=[CH:51][CH:52]=2)([SiH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[SiH2:29][C:30]2([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]2)([C:20]2[CH:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=2)[SiH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:54](C([Sn])=C(CCCC)CCCC)[CH2:55]CC.[C:69]1(C)C=CC=C[CH:70]=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:1]([C:5]1([SiH2:11][C:12]([O:27][C:28]([C:47]2[CH:48]=[N:49][C:50]([CH:69]=[CH2:70])=[CH:51][CH:52]=2)([SiH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[SiH2:29][C:30]2([C:36]([CH3:39])([CH3:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]2)([C:20]2[CH:21]=[N:22][C:23]([CH:54]=[CH2:55])=[CH:24][CH:25]=2)[SiH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 53438229Tri(butyl)vinyltinHCID 137328927HCID 137328927, compound

Product 1

HCID 137328926HCID 137328926, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
120 °C

Procedure

After dissolving 1-(tert-butyl)-1,1-diphenylsilyl [(6-chloro-3-pyridyl)methyl]ether (20 g, 52.3 mmol) in toluene (104 ml) and degassing the solution, tetrakis(triphenylphosphine)palladium (3.0 g, 2.6 mmol) and tributylvinyltin (16.5 ml, 56.5 mmol) were added under a nitrogen stream and the mixture was heated to reflux at 120° C. for 7 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (17.46 g) as a colorless oil. (89.3% yield)

Workup

  1. additionwere added under a nitrogen stream
  2. temperaturethe mixture was heated
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2049d08e2f0f44768a104c9469b735ce
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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