Diisopropylethylamine → (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-bicyclo[2.2.1]hept-2-yl-amine

Temperatur

110 °C

A mixture of 1-benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (0.92 g, 2.7 mmol), bicyclo[2.2.1]hept-2-ylamine (0.36 ml, 3.0 mmol), diisopropylethylamine (0.62 ml, 3.5 mmol) in propan-2-ol (12 ml) was heated at 110° C. in a microwave reactor for 20 min. The mixture was then cooled to 25° C. and was partitioned between water (200 ml) and EtOAc (2×200 ml). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated under reduced pressure. Purification of the resulting yellow oil by column chromatography on silica gel (gradient: 0 to 60% EtOAc in heptanes) afforded (1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-bicyclo[2.2.1]hept-2-yl-amine (1.1 g, 98%) as a yellow solid. TLC: 50% EtOAc in heptanes; Rf=0.66). This material was used in the next step below without additional characterization.

1. temperatureThe mixture was then cooled to 25° C.
2. customwas partitioned between water (200 ml) and EtOAc (2×200 ml)
3. dry with materialThe combined organic layers were dried over MgSO4
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customPurification of the resulting yellow oil by column chromatography on silica gel (gradient: 0 to 60% EtOAc in heptanes)

ORD-Eintrag

ord-f114f67c1a5c457aa097eb15c14998d8

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08461328B2