ChemicalBook CAS DataBase List METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-3-CARBOXYLATE

METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-3-CARBOXYLATE synthesis

4synthesis methods

Product Name:METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-3-CARBOXYLATE
CAS Number:116325-17-8
Molecular formula:C16H13NO4S
Molecular Weight:315.34

942-24-5
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98-09-9
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METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-3-CARBOXYLATE

116325-17-8
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Yield:116325-17-8 92%

Reaction Conditions:

with sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate in dichloromethane;water at 0 - 20; for 4.66667 h;

Steps:

1a 1-Benzenesulfonyl-1H-indole-3-carboxylic acid methyl ester

To a stirred solution of a suitable commercially available methyl indole-3-carboxylate (10 g, 57.1 mmol), tetrabutylammonium hydrogen sulfate (1.94 g, 5.71 mmol), and sodium hydroxide (22.8 g, 0.571 mmol) in a mixture solvent of CH₂Cl₂ (100 mL) and water (100 mL) at 0° C. was added benzenesulfonyl chloride (7.66 mL, 60.0 mmol). After 10 min at 0° C., the reaction was warmed to room temperature and stirred for an additional 4.5 h. The organic layer was separated and the aqueous layer was extracted with CH₂Cl₂ (50 mL). The combined organic layers were washed with brine, dried (MgSO₄), and concentrated in vacuo. The residue was triturated with diethyl ether and dried to give 16.8 g (92%) of compound 1a. ¹H NMR (400 MHz, DMSO-d₆) δ 8.46 (s, 1H), 8.16 (m, 2H), 8.05 (m, 1H), 8.00 (m, 1H), 7.76 (m, 1H), 7.46 (m, 2H), 7.47-7.39 (m, 2H), 3.88 (s, 3H) ppm; MS (m/e) 316 (M+1).

References:

US2007/299061,2007,A1 Location in patent:Page/Page column 9-10

67-56-1 Synthesis