Compound 27
4-(azidomethyl)-N-(3-cyano-4-methyl-1H-indol-7-yl)benzenesulfonamide
From: Structural basis of indisulam-mediated RBM39 recruitment to DCAF15 E3 ligase complex
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InChIKey OSSHJLMITRBVSF-UHFFFAOYSA-N
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To solution of 4-(bromomethyl)-N-(3-cyano-4-methyl-1H-indol-7-yl)benzenesulfonamide (26) (250 mg, 0.618 mmol) in DMF (Volume: 2 mL), NaN3 (201 mg, 3.09 mmol) was added, followed by TBAI (45.7 mg, 0.124 mmol). The reaction was treated at 120oC for 0.5 hr under microwave. The reaction was extracted between H2O and ethylacetate. Combined all the organics, dried, concentrated and purified over SiO2 with 40% ethylacetate/heptane to afford 4-(azidomethyl)-N-(3-cyano-4-methyl-1H-indol-7-yl)benzenesulfonamide (27) (200mg, 88%). LC-MS: m/z = 365.1 [M-H+]. 1H NMR (400 MHz, Chloroform-d) δ 7.85 (t, J = 3.1 Hz, 1H), 7.63 (dd, J = 8.4, 1.8 Hz, 2H), 7.39 (t, J = 8.6 Hz, 2H), 7.10 - 6.83 (m, 1H), 6.81 - 6.67 (m, 1H), 4.45 (d, J = 2.5 Hz, 2H), 2.77 - 2.69 (m, 3H)
