Potassium Carbonate → N-(4-(difluoromethoxy)phenyl)-6-vinylpyridazin-3-amine

HRID 77491

반응식

HRID 77491 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH:16]([F:18])[F:17])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:19](B1OC(C)(C)C(C)(C)O1)=[CH2:20].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[F:17][CH:16]([F:18])[O:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:5]2[N:6]=[N:7][C:2]([CH:19]=[CH2:20])=[CH:3][CH:4]=2)=[CH:10][CH:11]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 432354486-chloro-N-(4-(difluoromethoxy)phenyl)pyridazin-3-amine

생성물 1

HCID 86679785N-(4-(difluoromethoxy)phenyl)-6-vinylpyridazin-3-amine수율 61.9%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

To a solution of 6-chloro-N-(4-(difluoromethoxy)phenyl)pyridazin-3-amine (0.2 g, 0.736 mmol) in dioxane and water mixture were added vinylboronic acid pinacol ester (0.146 mL, 1.104 mmol), and K2CO3 (0.305 g, 2.209 mmol). The mixture was flushed for 15 min with nitrogen. PdCl2 (dppf)-CH2Cl2 adduct (0.060 g, 0.074 mmol) was then added and the reaction mixture heated at 80° C. for 18 h. The reaction mixture was filtered through a pad of celite, washed with ethyl acetate and purified by flash chromatography on silica gel using ethyl acetate in hexane to give N-(4-(difluoromethoxy)phenyl)-6-vinylpyridazin-3-amine as a white solid (0.12 g, 59%). 1HNMR 400 MHz, DMSO-d6: δ ppm 5.47 (d, J=1.20 Hz, 1H), 6.06 (dd, J=0.80, 23.80 Hz, 1H), 6.84-7.38 (m, 5H), 7.75-7.82 (m, 3H), 9.42 (s, 1H).

후처리

  1. customThe mixture was flushed for 15 min with nitrogen
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. washwashed with ethyl acetate
  4. custompurified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-70a27a3b47514ec89815ce94e3d224e7
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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