Реакция #45418

Уравнение реакции

solution

3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

N-iodosuccinimide

→

desired product

Выход 75.0%

7-iodo-3-(4-phenoxyphenyl)thieno[3,2-c]pyridin-4-amine

Выход 75.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated to half the original volume
2. 2
   workup.ADDITIONpoured into 5% sodium thiosulfate (400 mL)
3. 3
   ФильтрацияThe mixture was filtered
4. 4
   Промывкаthe filter cake was washed with water
5. 5
   Другоеdried
6. 6
   workup.DISSOLUTIONThe solids were dissolved in dichloromethane (300 mL)
7. 7
   workup.ADDITIONtreated with silica gel (80 g)
8. 8
   Концентрированиеconcentrated
9. 9
   Другоеchromatographed with ethyl acetate/heptane (1:6)

Методика

A solution of Example 219B (5 g, 15.7 mmol) in DMF (100 mL) was treated with N-iodosuccinimide (4.23 g, 18.8 mmol), stirred at ambient temperature for 2 hours, concentrated to half the original volume, and poured into 5% sodium thiosulfate (400 mL). The mixture was filtered and the filter cake was washed with water and dried. The solids were dissolved in dichloromethane (300 mL), treated with silica gel (80 g), and concentrated. The residue was transferred to a silica gel column (600 g) and chromatographed with ethyl acetate/heptane (1:6) to provide 5.2 g (75%) of the desired product. 1H NMR (CD2Cl2, 400 MHz) δ 7.95 (s, 1H), 7.33-7.29 (m, 4H), 7.12 (s, 1H), 7.10 (t, 1H), 7.02-6.99 (m, 4H), 4.76 (br s, 1H); 13C NMR (CD2Cl2, 400 MHz) δ 158.4, 156.8, 154.7, 154.4, 148.6, 138.4, 131.3, 131.2, 130.4, 124.4, 122.9, 120.0, 119,9, 118.8, 72.0.

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