Diisopropylamine → Thiazole, 2-[(trimethylsilyl)ethynyl]-

HRID 2428067Notes

Reaction equation

C(NC(C)C)(C)C.I[C:9]1[S:10][CH:11]=[CH:12][N:13]=1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16]>[Cu]I.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.O1CCCC1>[CH3:14][Si:15]([C:18]#[C:19][C:9]1[S:10][CH:11]=[CH:12][N:13]=1)([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

Copper(I)iodide (38 mg, 0.20 mmol), dichlorobis(triphenylphosphine)palladium(II) (250 mg, 0.40 mmol) and N,N-diisopropylamine (1.40 g, 14 mmol) were added to a solution of 2-iodothiazole (1.50 g, 7.0 mmol; prepared as described in J. Org. Chem. 1988, 53, 2489) and dry tetrahydrofuran (50 mL). The reaction mixture was degassed and trimethylsilylacetylene (1.40 g, 14 mmol) was added in two portions under nitrogen atmosphere. The reaction was heated to 50° C. for 12 h. The formed precipitate and separated palladium were removed by filtration through a short path of silica gel. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (silica gel Fluka 60: hexane/ethyl acetate 98:2-90:10) yielding 2-(trimethylsilylethynyl)thiazole as yellow oil.

Workup

customThe reaction mixture was degassed
customThe formed precipitate and separated palladium
customwere removed by filtration through a short path of silica gel
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by column chromatography (silica gel Fluka 60: hexane/ethyl acetate 98:2-90:10)

Sources & evidence

ORD record: ord-380882e4496a4bcf83386f1602873379
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968723B2

Reaction notes

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