5-Methoxyindoleacetic acid → HCID 177711155, compound

Participants

Reaction Steps

Step 2 (A): To a mixture of 2-(5-methoxy-1H-indol-3-yl)acetic acid (205 mg, 1.0 mmol)) and CH2Cl2/CH3CN/DIPEA (4.0 mL/0.5 mL/0.5 mL) was added HATU (418 mg, 1.1 mmol). The mixture was stirred at rt for 5 min, and then N-Boc-S-methylisothiourea (preparation C, 190 mg, 1.0 mmol) was added. The reaction was stirred at rt overnight. The resulting crude product was purified by silica gel chromatography to give 280 mg (yield 74%) of tert-butyl N-Boc-S-methylisothiourea-(2-(5-methoxy-1H-indol-3-yl)acetyl)(methylthio)-carbonoimidoylcarbamate. MS (ESI) (M+H)+=378.08. 1H-NMR (500 MHz, CDCl3) δ 7.22 (d, J=8.85 Hz, 1 H), 7.13 (s, 1 H), 6.92-6.99 (m, 1 H), 6.85 (dd, J=8.70, 2.29 Hz, 1 H), 3.83 (s, 5 H), 2.31 (s, 3 H), 1.26-1.51 (m, 9 H).

Provenance & Evidence