Tris(propan-2-yl)silanethiol → HCID 69023603, compound

HRID 1866801Notes

Reaction equation

HRID 1866801 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1Br)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[CH:65]([Si:68]([CH:73]([CH3:75])[CH3:74])([CH:70]([CH3:72])[CH3:71])[SH:69])([CH3:67])[CH3:66]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:19])[N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1[S:69][Si:68]([CH:70]([CH3:72])[CH3:71])([CH:73]([CH3:75])[CH3:74])[CH:65]([CH3:66])[CH3:67])[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 3435097Tris(propan-2-yl)silanethiolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 23676156Sodium t-butoxideHCID 69025407HCID 69025407, compound

Product 1

HCID 69023603HCID 69023603, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

[2-(2-Bromo-5-fluoro-phenyl)-ethyl]-methyl-carbamic acid tert-butyl ester (3.0 g, 9.03 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.10 g, 11.7 mmol), triisopropylsilanethiol (1.90 g, 9.93 mmol) and dry toluene (15 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 160° C. for 15 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (1:10). This furnishes 1.6 g (40%) of the title compound as an oil, which is used in the next step without further purification.

Workup

  1. customThe reaction vessel is sealed
  2. temperatureUpon cooling the mixture
  3. additionis poured onto a plug of silica
  4. washthe product is eluted with ethyl acetate-heptane (1:10)
  5. customThis furnishes 1.6 g (40%) of the title compound as an oil, which is used in the next step without further purification

Sources & evidence

ORD record
ord-bc8f80688e124ecfb5dfb5baece01b18
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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