Potassium Carbonate → HCID 86669907, 화합물

HRID 1506437

반응식

HRID 1506437 반응식
Br[CH2:2][C:3]#[C:4][C:5]1[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:7][N:6]=1.[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[C:23]([OH:29])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[C:23]([O:29][CH2:2][C:3]#[C:4][C:5]2[C:9]([C:10]([F:13])([F:12])[F:11])=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[O:7][N:6]=2)[CH:22]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 40660194-Bromo-2-hydroxybenzaldehydeHCID 67167391HCID 67167391, 화합물

생성물 1

HCID 86669907HCID 86669907, 화합물수율 75%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 3-(3-bromoprop-1-ynyl)-5-phenyl-4-(trifluoromethyl)isoxazole (Preparation 62C, 0.219 g, 0.663 mmol) and 4-bromo-2-hydroxybenzaldehyde (0.133 g, 0.663 mmol) in dimethylformamide (2.0 mL) at room temperature was added potassium carbonate (0.115 g, 0.829 mmol). The reaction mixture was stirred at room temperature for 3 h, diluted with ethyl acetate (75 mL), washed with a 10% aqueous solution of lithium chloride (2×25 mL), and washed with brine (25 mL). The organic layer was collected, and the combined aqueous phases were extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a tan solid which was triturated with methanol with sonication to give 4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde (0.223 g, 0.495 mmol, 75% yield) as a white solid. The product had an HPLC ret. time=3.28 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=451.92. 1H NMR (500 MHz, CDCl3) δ ppm 5.12 (s, 2H), 7.28 (d, J=8.32 Hz, 1H), 7.34 (d, J=1.66 Hz, 1H), 7.51-7.55 (m, 2H), 7.56-7.61 (m, 1H), 7.72 (d, J=7.21 Hz, 2H), 7.75 (d, J=8.32 Hz, 1H), and 10.44 (s, 1H).

후처리

  1. washwashed with a 10% aqueous solution of lithium chloride (2×25 mL)
  2. washwashed with brine (25 mL)
  3. customThe organic layer was collected
  4. extractionthe combined aqueous phases were extracted with ethyl acetate (2×25 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure
  7. customafforded a tan solid which
  8. customwas triturated with methanol with sonication

출처 및 근거

ORD 기록
ord-b5aa8a288b1f4703bb88a22fbd2b389e
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216972B2

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