Isopropyl iodide → HCID 66876886, 화합물

HRID 1666418노트

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HRID 1666418 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1.[CH:29](I)([CH3:31])[CH3:30].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH:29]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=2)[CH:12]=[C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15][CH2:14]2)=[N:6][CH:7]=1)([CH3:31])[CH3:30]

참가 물질

5

반응물 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

생성물 1

HCID 66876886HCID 66876886, 화합물수율 75.5%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of tert-butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (0.6 g, 1.56 mmol) in acetone (5 mL) cooled to 0° C. was added isopropyliodide (0.33 g, 1.96 mmol) and K2CO3 (0.43 g, 3.12 mmol). The reaction mixture was stirred at 80° C. overnight. The reaction mixture was evaporated to dryness and water (10 mL) was added and the mixture was extracted with ethyl acetate three times. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated to dryness under reduced pressure. The residue was purified by silica gel column chromatography (1:19 acetone:hexane) to give the title compound (0.5 g, 75%). 1H NMR (500 MHz, CDCl3): δ 7.86 (d, J=3.3 Hz, 1H), 7.28 (m, 2H), 6.96 (d, J=7.5 Hz, 1H), 6.91 (m, 2H), 6.84 (d, J=8.5 Hz, 1H), 6.32 (s, 1H), 4.45 (m, 1H), 3.49 (m, 2H), 3.38 (m, 2H), 2.45 (m, 2H), 2.31 (m, 2H), 1.47 (s, 9H), 1.33 (d, J=6 Hz, 6H); m/z (425.2, M+ H+).

후처리

  1. customThe reaction mixture was evaporated to dryness and water (10 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate three times
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:19 acetone:hexane)

출처 및 근거

ORD 기록
ord-d4df9589f6104204a37796e0401e303a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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