反応 #1973969

反応方程式

product

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

sodium carbonate

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

→

title compound

収率 11.0%

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

収率 11.0%

溶媒

toluene

ethanol

反応条件

後処理

1. 1
   その他microwaved at 100° C. for 30 min
2. 2
   温度The mixture was cooled
3. 3
   その他partitioned with ethyl acetate and 1M HCl
4. 4
   洗浄The organic layer was washed with saturated sodium bicarbonate, brine
5. 5
   乾燥dried with sodium sulfate
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他The residue was chromatographed on silica eluting with ethyl acetate/hexane (2:3 to 4:1)

実験手順

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)+.

出典