Potassium Carbonate → 2-Propyl-3-propyl-5-fluoro-1H-indole

HRID 2217772

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1[NH2:10].[CH3:16][CH2:17][CH2:18][C:19]#[C:20][CH2:21][CH2:22][CH3:23]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.CC(P(C(C)(C)C)C1[CH-]C=CC=1)(C)C.[Fe+2].CN1C(=O)CCC1>[CH2:18]([C:19]1[NH:10][C:9]2[C:8]([C:20]=1[CH2:21][CH2:22][CH3:23])=[CH:14][C:13]([F:15])=[CH:12][CH:11]=2)[CH2:17][CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

A 50 mL three neck flask was charged with palladium acetate (22.4 mg, 0.1 mmol), dtbpf (94 mg, 0.2 mmol), potassium carbonate (690 mg, 5 mmol), 2-bromo-4-fluoroaniline (380 mg, 2 mmol), 4-octyne (264 mg, 2.4 mmol) and NMP (10 ml). The mixture was purged with argon and heated to 130° C. After 1 hr, the reaction mixture was cooled to rt. Ethyl acetate and water were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic phases were washed with water, brine and dried with MgSO4. Removal of the solvents and purification of the crude by column chromatography afforded the desired product as yellow oil (355 mg, containing 4.3 wt % AcOEt). The corrected yield was 77.6%.

Aufarbeitung

customThe mixture was purged with argon
temperaturethe reaction mixture was cooled to rt
additionEthyl acetate and water were added
customThe organic layer was separated
extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic phases were washed with water, brine
dry with materialdried with MgSO4
customRemoval of the solvents and purification of the crude by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-3a2c616e16f14c24b8bb67d401799729
Quelldatensatz: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07408076B2

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