Реакция #1973969

Уравнение реакции

product

N-(6-bromonaphthalen-2-yl)methanesulfonamide

sodium carbonate

1-(3,5-diiodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione

→

title compound

Выход 11.0%

N-(6-(5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-iodo-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide

Выход 11.0%

Растворители

toluene

ethanol

Условия реакции

Обработка

1. 1
   Другоеmicrowaved at 100° C. for 30 min
2. 2
   ТемператураThe mixture was cooled
3. 3
   Другоеpartitioned with ethyl acetate and 1M HCl
4. 4
   ПромывкаThe organic layer was washed with saturated sodium bicarbonate, brine
5. 5
   Сушкаdried with sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Другоеevaporated
8. 8
   ДругоеThe residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1)

Методика

A mixture of the product from Part B 1-(3,5-diiodo-4-methoxyphenyl)pyrimidine-2,4(1H,3H)-dione (118 mg, 0.25 mmol), the product from Example 2A, Part B (87 mg, 0.25 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride CH2Cl2 complex (10.21 mg, 0.013 mmol) and sodium carbonate (0.250 ml, 0.25 mmol) in toluene (1.0 ml) and ethanol (1.0 ml) was sparged with nitrogen for 5 min and microwaved at 100° C. for 30 min. The mixture was cooled and partitioned with ethyl acetate and 1M HCl. The organic layer was washed with saturated sodium bicarbonate, brine, dried with sodium sulfate, filtered and evaporated. The residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1) to give the title compound (16 mg, 11%). 1H NMR (300 MHz, DMSO-D6) δ ppm 3.08 (s, 3 H) 3.35 (s, 3 H) 5.67 (d, J=8.09 Hz, 1 H) 7.42 (dd, J=8.82, 2.21 Hz, 1 H) 7.59 (d, J=2.57 Hz, 1 H) 7.73 (m, 2 H) 7.81 (d, J=8.09 Hz, 1 H) 7.95 (m, 3 H) 8.09 (s, 1 H) 10.06 (s, 1 H) 11.47 (s, 1 H). MS (ESI−) m/z 562 (M−H)+.

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