Compound 7
(R)-methyl (1-(5-bromo-2-(4-methylphenylsulfonamido)phenyl)-2-methyl-3H-benzo[e]indol-3-yl)carbamate
From: Organocatalytic asymmetric arylation of indoles enabled by azo groups
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Compound data: CIF
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
In a 5 ml vial equipped with 4d (84.8 mg, 0.2 mmol, 99% ee), pyridine (2 mL) and then TsCl (53.2 mg, 0.3 mmol) was added. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was evaporated in vacuo. Crude product was purified by chromatography on silica gel eluted with Et3N/PE (3/1 to 5/1) to afford 7 (100.7 mg, 87% yield) with 95% ee. 1H NMR (400 MHz, CDCl3) δ 8.42 – 8.02 (m, 1H), 7.90 – 7.68 (m, 2H), 7.66 – 7.44 (m, 3H), 7.43 – 7.23 (m, 3H), 7.22 – 6.94 (m, 3H), 6.93 – 6.71 (m, 2H), 6.70 – 6.08 (m, 1H), 4.05 – 3.52 (m, 3H), 2.29 – 2.12 (m, 3H), 2.11 – 1.84 (m, 3H). 13C NMR (100 MHz, CDCl3) (two indistinguishable rotamers) δ 155.9, 143.8, 135.5, 135.2, 134.7, 134.5, 134.3, 134.0, 133.3, 131.9, 130.3, 130.0, 129.3, 128.7, 128.5, 127.3, 127.0, 126.7, 126.2, 125.5, 124.4, 123.7, 123.6, 122.8, 122.1, 119.9, 118.1, 117.1, 109.7, 109.6, 106.9, 53.5, 21.5, 9.4. HRMS (ESI) calcd for [M+H] C28H25BrN3O4S, m/z: 578.0744, found: 578.0729. HPLC analysis: HPLC DAICEL CHIRALCEL AD-3, hexane/isopropanol = 85/15, 1.0 mL/min, λ = 254 nm, tR (minor) = 10.4 min, tR (major) = 13.9 min, ee = 95%.
