5-bromo-1-(p-toluenesulfonyl)-1H-indole synthesis
- Product Name:5-bromo-1-(p-toluenesulfonyl)-1H-indole
- CAS Number:96546-77-9
- Molecular formula:C15H12BrNO2S
- Molecular Weight:350.23
Yield:96546-77-9 100%
Reaction Conditions:
Stage #1: 5-Bromoindolewith sodium hydride in N,N-dimethyl-formamide at 0; for 1 h;
Stage #2: p-toluenesulfonyl chloride in N,N-dimethyl-formamide at 20; for 4.5 h;
Steps:
To a suspension of sodium hydride (60% dispersion in mineral oil, 2.448 g, 61.2 mmol) in DMF (150 mL), a solution of 5-bromo-lH-indole A.126 (10 g, 51 mmol) was added and the mixture was stirred at 0 0C for 1 hour. To the mixture was added a solution of p-TsCl (11.6695 g, 61.2 mmol) in DMF (50 mL) and the mixture was stirred at room temperature for 4.5 hours. The mixture was poured into water (500 mL) and the resulting precipitate was collected by suction filtration, washed with water (1 L), and dried to give 5-bromo-l-tosyl-lH-indole A.127 (18. g, quantitative) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.78 - 7.93 (5 H, m), 7.44 - 7.52 (1 H, m), 7.39 (2 H, d, J=8.1 Hz), 6.81 (1 H, d, J=3.7 Hz), 2.32 (3 H, s); Mass Spectrum (ESI) m/e = 350.0 [M+l (79Br)] and 352.0 [M+l (81Br)].
References:
WO2009/158011,2009,A1 Location in patent:Page/Page column 74
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