Tris(propan-2-yl)silanethiol → Methyl-(2-triisopropylsilanylsulfanyl-benzyl)-carbamic acid tert-butyl ester

HRID 493092

Reaction equation

[C:1]([O:5][C:6](=[O:17])[N:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1I)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[CH:24]([Si:27]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[SH:28])([CH3:26])[CH3:25]>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(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:17])[N:7]([CH3:8])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:28][Si:27]([CH:29]([CH3:31])[CH3:30])([CH:32]([CH3:34])[CH3:33])[CH:24]([CH3:25])[CH3:26])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 160 °C

Procedure

(2-Iodo-benzyl)-methyl-carbamic acid tert-butyl ester (3.0 g, 8.64 mmol), tris(dibenzylideneacetone)dipalladium (0) (79 mg, 0.086 mmol), bis(2-diphenylphosphinophenyl)ether (93 mg, 0.17 mmol), sodium tert-butoxide (1.10 g, 11.2 mmol), triisopropylsilanethiol (1.73 g, 9.07 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 (1:4). This procedure is repeated an additional 3 times to furnish a total of 13.7 g (97%) of the title compound as an oil which is used in the next step without further purification.

Workup

customThe reaction vessel is sealed
temperatureUpon cooling the mixture
additionis poured onto a plug of silica
washthe product is eluted with ethyl acetate-heptane (1:4)

Sources & evidence

ORD record: ord-b2416be841294e798e23e6aab34f8d16
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534791B2

Linked notes

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