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

HRID 585905ノート

反応式

HRID 585905 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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) δ7.39 (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=13.8,7.8Hz, 1H), 3.55 (m, 1H), 3.48 (bm, 4H), 1.19 (d, J=6.6 Hz, 3H); MS m/z 230 [M+H]+.

後処理

  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)

出典と根拠

ORDレコード
ord-df3b2428b578474492ea58f22cf629fa
出典データセット
uspto-grants-2005_08
特許番号
US06933392B2

反応ノート

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