4-Toluenesulfonyl chloride → 5-(2-fluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(2-fluorophenyl)-3-iodo-1H-pyrrolo[3,2-b]pyridine (227 mg, 0.671 mmol) in THF (7 mL) was treated with TsCl (141 mg, 0.738 mmol, Fluka) and solid NaOH (32.2 mg, 0.806 mmol, VWR). The reaction was stirred at 23° C. under N2. After 45 min, the solution was diluted with EtOAc (100 ml) and washed with brine (75 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 10-25% EtOAc/hexane), affording 5-(2-fluorophenyl)-3-iodo-1-tosyl-1H-pyrrolo[3,2-b]pyridine (238 mg, 72%). MS (ESI, pos. ion) m/z: 493.0 (M+1).

Provenance & Evidence