Реакция #306034

Уравнение реакции

K2CO3

product

2-isopropoxy-3-methoxy-6-(prop-1-ynyl)-N-trifluoroacetylaniline

3,4,5-trimethoxyphenyl iodide

→

title compound

Выход 64.0%

7-isopropoxy-6-methoxyl-2-methyl-3-(3,4,5-trimethoxybenzoyl)-1H-indole

Выход 64.0%

Условия реакции

Обработка

1. 1
   Другое1.62 mmol in anhydrous DMF (5 ml) was degassed under reduced pressure and saturated with CO gas
2. 2
   workup.ADDITIONballoon, then diluted to 50 ml with ethyl acetate
3. 3
   Промывкаwashed with water (3×15 ml), brine
4. 4
   Сушкаdried over anhydrous MgSO4
5. 5
   Фильтрацияfiltered off
6. 6
   Другоеfiltrate evaporated to dryness
7. 7
   ДругоеThe residue was purified by flash column chromatography (SiO2 CH2Cl2/ethyl acetate, 9:1)

Методика

A mixture of the product of Step C (0.171 g; 0.54 mmol), 3,4,5-trimethoxyphenyl iodide (0.191 g; 0.65 mmol), Cl2Pd(PPh3)2 (0.044 g; 0.063 mmol); dry K2CO3 (0.23 g; 1.62 mmol in anhydrous DMF (5 ml) was degassed under reduced pressure and saturated with CO gas. The resulting mixture was vigorously stirred overnight at room temperature under CO balloon, then diluted to 50 ml with ethyl acetate and washed with water (3×15 ml), brine and dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness. The residue was purified by flash column chromatography (SiO2 CH2Cl2/ethyl acetate, 9:1) to give the title compound (0.143 g; 64% yield) as a yellow solid. 1H-NMR (CDCl3) 1.27 (d, 6H, J=6.14 Hz); 2.51 (s, 3H); 3.79 (s, 6H); 3.85 (s, 3H); 3.90 (s, 3H); 4.69 (m, 1H, J=6.14 Hz): 6.76 (d, 1H, J=8.75 Hz); 7.04 (s, 2H); 7.11 (d, 1H, J=8.75 Hz); 8.83 (broad m, 1H).

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