Benzenesulfonyl chloride → 1h-Pyrrolo[2,3-b]pyridine,5-bromo-2,3-dihydro-1-(phenylsulfonyl)-

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Reaction Steps

To a 0° C. stirred solution of 5-bromo-azaindoline 5 (150 mg, 0.75 mmol) in N,N-dimethylacetamide (7 mL) was added in one portion 60% dispersion of NaH in mineral oil (38 mg, 0.94 mmol). After 0.5 h benzenesulfonyl chloride (0.12 mL, 0.94 mmol) in N,N-dimethylacetamide (1 mL) was added dropwise, and the mixture allowed to slowly warm to r.t. After 2 days the mixture was partitioned between AcOEt-brine. The aqueous layer was extracted with AcOEt (2×). The combined organic solutions were dried (MgSO4), filtered and concentrated. The residue was purified by preparative TLC (PTLC) with CH2Cl2 as eluent to afford the azaindoline 6 (21 mg, 8%) as a solid. 1H NMR (400 MHz; CDCl3) δ 3.04 (t, J=8.6 Hz, 2H), 4.08 (t, J=8.6 Hz, 2H), 7.45-7.51 (m, 3H), 7.56-7.60 (m, 1H), 8.08 (m, 2H), 8.18 (m, 1H).

Provenance & Evidence