Compound 9
4-(aminomethyl)-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 YYJILEGPDDMZAV-UHFFFAOYSA-N
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
To the solution of 4-(azidomethyl)-N-(3-cyano-4-methyl-1H-indol-7-yl)benzenesulfonamide (27) (680 mg, 1.856 mmol) in THF (Volume: 10 mL, Ratio: 10.00) and H2O (Volume: 1 mL, Ratio: 1.000), triphenylphosphine (730 mg, 2.78 mmol) was added. The reaction was treated at 60oC for 3hr. The reaction was extracted between H2O and ethylacetate. All organics were combined, dried, concentrated and purified over SiO2 with 10% MeOH/DCM to afford 4-(aminomethyl)-N-(3-cyano-4-methyl-1H-indol-7-yl)benzenesulfonamide (9) (500 mg, 79%). LC-MS: m/z = 341.2 [M+H+]. 1H NMR (400 MHz, Methanol-d4) δ 8.53 (s, 1H), 7.97 (s, 1H), 7.89 - 7.62 (m, 2H), 7.62 - 7.44 (m, 2H), 6.72 (dd, J = 7.7, 1.0 Hz, 1H), 6.47 (d, J = 7.6 Hz, 1H), 4.16 (s, 2H), 2.66 (d, J = 0.8 Hz, 3H).
