Reaktion #1974171

Reaktionsgleichung

methyl 3-amino-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate

1-Methoxy-1-oxo-1λ5 phosphinan-4-one

dibutyltin dichloride

phenylsilane

→

title compound

Ausbeute 85.0%

Methyl 5-(3,3-Dimethyl-but-1-ynyl)-3-(1-methoxy-1-oxo-1λ5phosphinan-4-ylamino)-thiophene-2-carboxylate

Ausbeute 85.0%

Lösungsmittel

THF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between water and ethyl acetate
2. 2
   ExtraktionThe aqueous phase was extracted with ethyl acetate
3. 3
   WaschenThe combined organic layers were washed with 5% LiCl and brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

A solution of methyl 3-amino-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate (474 mg, 2 mmol) and 1-Methoxy-1-oxo-1λ5 phosphinan-4-one (390 mg, 2.4 mmol) in THF (1 mL) and DMF (1 mL) was treated with dibutyltin dichloride (60 mg, 0.2 mmol). After 5 min, phenylsilane (272 μL, 2.2 mmol) was added, and the mixture was stirred for one hour at room temperature and then partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with 5% LiCl and brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography using EtOAc:Hexanes as eluent to provide 650 mg (85%) of title compound: MS (m/z) 384.0 [M+H]−; HPLC retention time: 4.463 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

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