Yield:-

Reaction Conditions:

Stage #1: vinyl magnesium bromide;2-chloro-5-methoxynitrobenzene in tetrahydrofuran at -40;
Stage #2: with ammonium chloride in tetrahydrofuran;water;

Steps:

11

Description 11. 7-Chloro-4-(methyloxy)-1H-indole (D11) To a solution of 4-chloro-3-nitroanisole (6.0 g, 32.0 mmol) in tetrahydrofuran (140 ml.) at -4O⁰C was added vinylmagnesium bromide (1 M in tetrahydrofuran, 112 ml_, 112.0 mmol). The mixture was stirred at -4O⁰C for 1.5 hours and then quenched by the addition of saturated aqueous ammonium chloride solution (150 ml_). The reaction mixture was allowed to warm to room temperature and then the product extracted into ethyl acetate (x2). The combined organic layers were dried over magnesium sulphate, filtered and concentrated at reduced pressure. The product was purified by silica gel chromatography eluting with 2-15% ethyl acetate in hexane to yield the title compound (D11 ), (1.67 g). LC-MS: MH⁺ = 182 (C₉H₈CINO = 181)

References:

WO2009/103710,2009,A1 Location in patent:Page/Page column 19