Tetrahydrofuran → 1-(2-Aminopropyl)-1,4-dihydro-indeno[1,2-c]pyrazol-6-ol

HRID 1816464노트

반응식

HRID 1816464 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:16](=[CH:17][CH:18]=1)[C:8]1[N:9]([CH2:12][CH:13]([NH2:15])[CH3:14])[N:10]=[CH:11][C:7]=1[CH2:6]2.[B-](Br)(Br)(Br)[S+](C)C.C1COCC1.C([O-])(O)=O.[Na+]>ClCCCl>[NH2:15][CH:13]([CH3:14])[CH2:12][N:9]1[C:8]2[C:16]3[C:5]([CH2:6][C:7]=2[CH:11]=[N:10]1)=[CH:4][C:3]([OH:2])=[CH:18][CH:17]=3

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4181510Tribromoborane-methyl sulfideHCID 223383072-(6-Methoxy-4H-indeno[1,2-c]pyrazol-1-yl)-1-methylethylamine

생성물 1

HCID 1354860361-(2-Aminopropyl)-1,4-dihydro-indeno[1,2-c]pyrazol-6-ol수율 13.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of the product from Step D (0.56 g, 0.23 mmol) in 1,2-dichloroethane (10 mL) was added boron tribromide-methylsulfide complex in THF solution (1.0M, 0.5 mL, 0.5 mmol) and the solution heated to reflux for 16 h. The solution was allowed to cool, poured into aqueous NaHCO3, extracted with chloroform (2×20 mL), dried (Na2SO4) and concentrated. The crude product was purified by chromatography (silica, 20% methanol in dichloromethane) to give a solid (0.007 g, 13%): 1H NMR (CDCl3) δ 7.39 (m, 2H), 7.00 (s, 1H), 6.79 (dd, J=8.4, 2.4 Hz, 1H), 4.30 (dd, J=13.8, 4.8 Hz, 1H), 4.14 (dd, J=13.8, 7.8 Hz, 1H), 3.55 (m, 1H), 3.48 (bm, 4H), 1.19 (d, J=6.6 Hz, 3H); MS m/z 230 [M+H]+.

후처리

  1. temperaturethe solution heated
  2. temperatureto reflux for 16 h
  3. temperatureto cool
  4. extractionextracted with chloroform (2×20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica, 20% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-5be2650b95374d2f996876ca16654edf
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884816B2

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