Pyridine, 3-methyl-4-nitro-, 1-oxide → 5-Azaindole

This compound is prepared in a procedure similar to that described by J. R. Dormoy and A. Heymes in Tetrahedron, 1993, 49(14), 2885-2914. A stirred solution of 3-methyl-4-nitropyridine N-oxide (10.0 g, 65.0 mmol) and N,N-dimethylformamide diethyl acetal (14.5 g, 99 mmol) in DMF is placed in a preheated bath (90° C.) for 1.25 h, cooled and filtered. The filtercake is rinsed with a small amount of methanol and air-dried to give a purple-brown solid, 12.1 g. A portion of this solid (2.09 g, 10.0 mmol) is dissolved in ethanol (50 mL) and acetic acid (2 mL), treated with 10% palladium on carbon placed under 54 psi of hydrogen on a Parr shaker for 16 h and filtered through Celite. The filtrate is concentrated in vacuo and the concentrate is chromatographed (silica gel, 20:80 ethanol:EtOAc), followed by 50:50 ethanol:EtOAc as eluent) to afford the title 5-azaindole compound as a pink solid, 0.601 g (51% yield), identified by comparison of the NMR to literature (Can. J. Chem., 1969, 47, 3257).

1. customThis compound is prepared in a procedure similar to
2. temperaturecooled
3. filtrationfiltered
4. washThe filtercake is rinsed with a small amount of methanol
5. customair-dried
6. customto give a purple-brown solid, 12.1 g
7. filtrationfiltered through Celite
8. concentrationThe filtrate is concentrated in vacuo
9. customthe concentrate is chromatographed (silica gel, 20:80 ethanol:EtOAc)

ORD 기록

ord-7fba09ff289947278d0d188fe430b502

출처 데이터셋

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06800640B2