HCID 59238643, compound → HCID 59238778, compound

Participants

Reaction Steps

5-(bicyclo[2.2.1]hept-2-en-2-yl)-3-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 2 (63 mg, 0.146 mmol) in EtOH (1.50 mL) and 10% aqueous NaOH (0.75 mL), was deprotected as described in the general procedure A for the deprotection of 7-azaindoles by refluxing for 20 min. The reaction was quenched by addition of a saturated solution of NaHCO3 (15 mL) and the mixture was stirred for 20 minutes. It was extracted with EtOAc (3×15 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product purified by PTLC using EtOAc as the eluent to give (I-136) (24.8 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 1.16-1.25 (m, 2H), 1.32 (d, J=8.2 Hz, 1H), 1.59-1.63 (m, 1H), 1.80-1.89 (m, 2H), 3.04-3.08 (m, 1H), 3.42-3.45 (br s, 1H), 4.01 (s, 3H), 6.35 (d, J=3.1 Hz, 1H), 7.39 (d, J=2.3 Hz, 1H), 7.64 (s, 1H), 7.78 (d, J=0.5 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 8.49 (d, J=2.0 Hz, 1H), 10.09 (br s, NH, 1H).

Provenance & Evidence