Water → HCID 86692601, 화합물

HRID 1748661노트

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HRID 1748661 반응식
CC1(C)C(C)(C)OB([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:18])([F:17])[F:16])[CH2:11][CH:10]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35]([C:37]2[CH:38]=[N:39][N:40]([C:43]3[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][N:44]=3)[C:41]=2[CH3:42])=[O:36])=[CH:30][C:29]=1[CH3:53]>O1CCOCC1.C(OCC)(=O)C>[CH3:42][C:41]1[N:40]([C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:50])([F:52])[F:51])=[CH:45][N:44]=2)[N:39]=[CH:38][C:37]=1[C:35]([NH:34][C:31]1[CH:32]=[N:33][C:28]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([F:16])([F:17])[F:18])[CH2:11][CH:10]=2)=[C:29]([CH3:53])[CH:30]=1)=[O:36]

참가 물질

7

반응물 4

HCID 962Water2회HCID 10340Sodium CarbonateHCID 115653404,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)-1-cyclohexen-1-yl]-1,3,2-dioxaborolaneHCID 86692602HCID 86692602, 화합물

생성물 1

HCID 86692601HCID 86692601, 화합물수율 63.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

4,4,5,5-Tetramethyl-2-[4-(trifluoromethyl)cyclohex-1-en-1-yl]-[1,3,2] dioxaborolane (163 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (37 mg), sodium carbonate (144 mg) and water (1.0 ml) were added at room temperature to a solution of N-(6-bromo-5-methylpyridin-3-yl)-5-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]-1H-pyrazole-4-carboxamide (200 mg) described in Reference Example 189 in 1,4-dioxane (3.0 ml), and stirred at 100° C. under radiation of microwave for an hour. After completion of the reaction, water and ethyl acetate were added, filtered through Celite and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chloroform/methanol) to give the titled compound (146 mg) as a white solid.

후처리

  1. additionwere added
  2. filtrationfiltered through Celite
  3. extractionthe filtrate was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (chloroform/methanol)

출처 및 근거

ORD 기록
ord-e6832daeedfa484f92c6b5aca0a0122d
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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