Triphenylphosphine → ethyl 5-[2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethoxy]-1H-indole-2-carboxylate

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A solution of ethyl 5(hydroxy)-1H-indole-2-carboxylate (991 mg, 4.83 mmol) and 2-(5-methyl-2-phenyl-1,3-thiazol-4-yl)ethanol (1.06 g, 4.83 mmol) in tetrahydrofuran (30 +5 mL rinse) was added to a stirred mixture of triphenylphosphine (1.3 g, 4.9 mmol) and 1,1′-(azodicarbonyl)dipiperidine (1.2 g, 4.9 mmol) in tetrahydrofuran (10 mL). The reaction was stirred for 48 h and then diluted with ethyl acetate (200 mL). This solution was washed successively with water, 10% hydrochloric acid, and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. Flash chromatography of the residue over silica gel using 25% ethyl acetate/hexane gave 1.04 g (53%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) □ 10.40-10.55 (br s, 1 H), 7.89-7.95 (m, 2 H), 7.38-7.49 (m, 4 H), 7.19 (d, 1 H), 7.06-7.09 (m, 1 H), 6.95 (dd, 1 H), 4.30-4.40 (m, 4 H), 3.20 (t, 2 H), 2.51 (s, 3 H), 1.35 (t, 3 H); mass spectrometry gave MH+=407.1 (calc'd exact mass for C23H22N2O3S=406.14).

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