4-Aminoacetanilide → HCID 24877275, Verbindung

Temperatur

62 °C

A 25 mL reaction flask was charged with (3E)-6-bromo-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-1,3-dihydro-2H-indol-2-one (100 mg, 0.26 mmol), N-(4-aminophenyl)acetamide (46 mg, 0.31 mmol), dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (4.9 mg, 0.012 mmol), Pd2(dba)3 (4.8 mg, 0.0052 mmol), 1M LiHMDS in THF (0.83 mL, 0.83 mmol) and dry THF (10 mL). The mixture was purged with nitrogen and heated in 62° C. bath under nitrogen for 2 hours. After cooling to room temperature, the reaction mixture was quenched with 0.5 mL of 2M HCl, and diluted with ethyl acetate (100 mL). The solution was washed with saturated NaHCO3 (2×50 mL), brine (50 mL), and concentrated to give the crude product. Purification of the crude prduct by silica gel chromatography with a gradient of methanol in chloroform (5-10%) led to N-(3-{[(3E)-3-(5,5-dimethyl-4-morpholin-4-ylfuran-2(5H)-ylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]amino}phenyl)acetamide as a yellow solid. Yield: 20 mg, 17%.

1. customA 25 mL reaction flask
2. customThe mixture was purged with nitrogen
3. temperatureAfter cooling to room temperature
4. customthe reaction mixture was quenched with 0.5 mL of 2M HCl
5. additiondiluted with ethyl acetate (100 mL)
6. washThe solution was washed with saturated NaHCO3 (2×50 mL), brine (50 mL)
7. concentrationconcentrated

ORD-Eintrag

ord-c7d80ec3db5649b0ac87590211aa17e3

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367664B2