Tetrahydrofuran → HCID 67346331, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(1-benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (7.09 g, 11.4 mmol) and palladium on carbon (2.1 g, 10%, wet, Degussa, E101 NE/W) in a 4:1 mixture of THF and EtOH (100 ml) was stirred under a hydrogen atmosphere (2 balloons) at 50° C. for 6 h. The reaction mixture was cooled to 25° C. and was filtered through Celite. The Celite was washed with THF (2×25 ml), and the combined filtrate and washings were concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (gradient: 0 to 7% CH3OH in CH2Cl2) gave 3-(5-amino-1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-4-ylamino)-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester (5.76 g, 85%, purple foam) still containing some impurities. This material was used in the next step below without additional purification or characterization.

Provenance & Evidence