Iodine → 3-Iodo-4,5,6,7-tetrahydro-1H-indazole

HRID 246404노트

반응식

HRID 246404 반응식
[NH:1]1[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[C:3](C(O)=O)=[N:2]1.C(=O)(O)[O-].[Na+].[I-:18].[Na+].II>ClC(Cl)C.O.ClCCl>[I:18][C:3]1[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[NH:1][N:2]=1

참가 물질

8

반응물 4

HCID 807IodineHCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 6488524,5,6,7-Tetrahydro-1H-indazole-3-carboxylic acid

생성물 1

HCID 712807353-Iodo-4,5,6,7-tetrahydro-1H-indazole수율 79.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 63651,1-Dichloroethane용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 4,5,6,7-tetrahydro-1H-indazole-3-carboxylic acid (0.57 g, 3.43 mmol), and sodium bicarbonate (951 mg, 440 μL, 11.3 mmol) in dichloroethane (5 mL) and water (5 mL) were added in one portion sodium iodide (1.34 g, 8.92 mmol) and iodine (1.13 g, 4.46 mmol) and the mixture heated at to 100° C. (oil bath temperature) with vigorous stirring for 24 h. After cooling to 25° C. the mixture was diluted with dichloromethane, then washed with 10% Na2S2O3 and saturated NaHCO3. The organic phases were combined, dried (MgSO4) and concentrated to an off-white solid which was purified by chromatography (115 g column, 50 μm from Analogix, 0 to 5% over 15 min (MeOH containing 10% ammonium hydroxide)/dichloromethane to give 3-iodo-4,5,6,7-tetrahydro-1H-indazole (674 mg, 2.72 mmol, 79.2%) as a white solid. MS (M+H)+=249 (>90% purity); 1H NMR (CDCl3) δ: 2.75 (t, J=5.7 Hz, 2H), 2.35 (t, J=5.7 Hz, 2H), 1.61-1.90 (m, 4H).

후처리

  1. temperatureAfter cooling to 25° C. the mixture
  2. washwashed with 10% Na2S2O3 and saturated NaHCO3
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to an off-white solid which
  5. customwas purified by chromatography (115 g column, 50 μm from Analogix, 0 to 5% over 15 min (MeOH containing 10% ammonium hydroxide)/dichloromethane

출처 및 근거

ORD 기록
ord-7c9f1b094b114b7496522b6c6007a384
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

반응 노트

불러오는 중…