Nitrogen → 1-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-3-nitro-1H-pyrazole

HRID 2064935

반응식

HRID 2064935 반응식
N#N.[N+:3]([C:6]1[NH:10][N:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][CH2:20][CH2:21][C:22]1([CH3:27])[O:26][CH2:25][CH2:24][O:23]1>C(C#N)(C)=O.CC(=O)OCC.O>[CH3:27][C:22]1([CH2:21][CH2:20][CH2:19][CH2:18][N:9]2[CH:8]=[CH:7][C:6]([N+:3]([O-:5])=[O:4])=[N:10]2)[O:26][CH2:25][CH2:24][O:23]1

참가 물질

8

반응물 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 1234193-NitropyrazoleHCID 5600132-(4-Bromobutyl)-2-methyl-1,3-dioxolane

생성물 1

HCID 669283351-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-3-nitro-1H-pyrazole

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 694302-Oxopropiononitrile용매2회

반응 조건

온도
80 °C

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-nitro-1H-pyrazole (2.97 g, 18.68 mmol) and Cs2CO3 (6.67 g, 26.22 mmol) in AcCN (27.0 mL) was treated with a solution of 2-(4-bromo-butyl)-2-methyl-[1,3]dioxolane (5.85 g, 26.22 mmol) in AcCN (27.0 mL). The reaction mixture was stirred at 80° C. for 2.5 h. Water (100 mL) and EA (200 mL) were added to the cooled reaction mixture. The aq. layer was extracted with EA (100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (60:40 hept-EA) gave the title compound. TLC: rf (60:40 hept-EA)=0.17. LC-MS-conditions 02: tR=0.89 min; [M+H]+=256.32. 1H NMR (400 MHz, CDCl3) δ 1.31 (s, 3H), 1.39-1.50 (m, 2H), 1.67-1.75 (m, 2H), 1.92-2.02 (m, 2H), 3.88-3.94 (m, 2H), 3.94-4.00 (m, 2H), 4.22 (t, J=7.0 Hz, 2H), 6.91 (d, J=2.3 Hz, 1H), 7.46 (d, J=2.3 Hz, 1H).

후처리

  1. extractionThe aq. layer was extracted with EA (100 mL)
  2. dry with materialextracts were dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (60:40 hept-EA)

출처 및 근거

ORD 기록
ord-37768abc908d4f96b70773ef81fcb7bd
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288419B2

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