Sodium Carbonate → 5-bromo-2-(1-isopropyl-1H-pyrazol-5-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595649노트

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HRID 595649 반응식
[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[CH:22]([N:25]1[C:29](B(O)O)=[CH:28][CH:27]=[N:26]1)([CH3:24])[CH3:23].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([C:29]3[N:25]([CH:22]([CH3:24])[CH3:23])[N:26]=[CH:27][CH:28]=3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 23139440(1-Isopropyl-1H-pyrazol-5-yl)boronic acidHCID 903324695-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903333365-bromo-2-(1-isopropyl-1H-pyrazol-5-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide수율 50%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

To a solution of 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (50 mg, 0.12 mmol), (1-isopropyl-1H-pyrazol-5-yl)boronic acid (23 mg, 0.12 mmol) and Na2CO3 (22 mg, 0.25 mmol) in 1,4-dioxane (0.5 mL) and water (0.05 mL) was added Pd (dppf)Cl2 (10 mg) under nitrogen. The mixture was heated at 100° C. for 4 hour and filtered through the Celite pad. The filtrate was extracted with EtOAc, and then the combined organic phase was washed with brine, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by the prep-TLC (PE:EA=1:1) to give 5-bromo-2-(1-isopropyl-1H-pyrazol-5-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (25 mg, yield: 50%). 1H-NMR (CDCl3, 400 MHz) δ 8.50 (s, 1H), 7.66 (s, 1H), 7.64 (s, 1H), 6.58 (d, J=2.0 Hz, 1H), 5.74 (d, J=3.6 Hz, 1H), 4.45˜4.52 (m, 1H), 3.28 (s, 3H), 3.04 (s, 3H), 2.82 (d, J=4.8 Hz, 3H), 1.51 (s, 6H). MS (M+H)+: 469/471.

후처리

  1. filtrationfiltered through the Celite pad
  2. extractionThe filtrate was extracted with EtOAc
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by the prep-TLC (PE:EA=1:1)

출처 및 근거

ORD 기록
ord-d8d9df6937664d5da6efe3415a596f9d
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09243002B2

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