Triethylamine → (4-Methyl-5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 1009032Notes

Reaction equation

[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][C:10](I)=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:23]([Si:25]([CH3:28])([CH3:27])[CH3:26])#[CH:24].[NH4+].[Cl-]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[S:9][C:10]([C:24]#[C:23][Si:25]([CH3:28])([CH3:27])[CH3:26])=[C:11]([CH3:13])[N:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 32 °C

Procedure

Under a stream of Ar the above prepared (5-iodo-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.913 g, 2.68 mmol) was dissolved in 17 mL of acetonitrile and treated successively with triethylamine (1.12 mL, 3 eq.), Cul (0.051 g, 0.1 eq.), (Ph3P)2PdCl2 (0.188 g, 0.1 eq.), and ethynyltrimethylsilane (1.11 mL, 3 eq.). The flask was closed with a septum and allowed to stir for 4 h at 32° C. The reaction mixture was then poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/ethyl acetate=85/15) gave finally 0.592 g of the title compound as light brown foam.

Workup

customThe flask was closed with a septum
extractiontwofold extracted with ethyl acetate
washwashed with water and brine
dry with materialdried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-3f802dda17a14e6a8429c1893c9b84c4
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07973051B2

Reaction notes

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