HCID 118232987, 화합물 → 3-(3-chloro-4-methyl-1H-pyrazol-1-yl)pyridine

HRID 1525781노트

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HRID 1525781 반응식
[Cl:1][C:2]1[CH:6]([CH3:7])[CH2:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1>C(#N)C.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:6]([CH3:7])=[CH:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1

참가 물질

4

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HCID 118232987HCID 118232987, 화합물

생성물 1

HCID 216244353-(3-chloro-4-methyl-1H-pyrazol-1-yl)pyridine수율 95%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매2회HCID 6342Acetonitrile용매

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온도
22 °C

실험 절차

To a solution of 3-(3-chloro-4-methyl-4,5-dihydro-1H-pyrazol-1-yl)pyridine (1.0 g, 5.0 mol) in acetonitrile (10.0 mL) at 0° C. was added manganese(IV) oxide (1.3 g, 15 mmol) portionwise over 10 minutes. The mixture was slowly warmed to 22° C. over 40 minutes and then heated to 40° C. overnight. After 20 hours, additional manganese(IV) oxide (0.44 g, 5.0 mmol) was added in one portion and the mixture was stirred for 1 hour. The mixture was cooled down and filtered. The filter cake was washed with acetonitrile (3×15 mL). The organic filtrate was dried and concentrated to afford the title compound as a light yellow solid (0.92 g, 95%): 1H NMR (400 MHz, CDCl3) δ 8.90 (dd, J=2.6, 0.8 Hz, 1H), 8.52 (dd, J=4.8, 1.5 Hz, 1H), 7.99 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.74 (q, J=0.9 Hz, 1H), 7.39 (ddd, J=8.3, 4.8, 0.8 Hz, 1H), 2.13 (d, J=0.9 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 147.26, 142.87, 139.53, 135.90, 126.53, 125.69, 123.84, 116.86, 22.47; EIMS m/z 193 ([M]+).

후처리

  1. temperatureheated to 40° C. overnight
  2. temperatureThe mixture was cooled down
  3. filtrationfiltered
  4. washThe filter cake was washed with acetonitrile (3×15 mL)
  5. customThe organic filtrate was dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9b5fe8c559d0493781d49805a98fdb4d
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085552B1

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