Tetrabutylammonium Fluoride → tert-Butyl 4-((1-(5-chloro-1H-indazol-7-yl)-2-fluoroethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

HRID 913949ノート

反応式

HRID 913949 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:14][CH2:15][C:16]3([C:29]4[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=4)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH2:12][F:13])[CH:10]=1)[NH:7][N:6](COCC[Si](C)(C)C)[CH2:5]2.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH:11]([O:14][CH2:15][C:16]3([C:29]4[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=4)[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[CH2:12][F:13])[CH:10]=1)[NH:7][N:6]=[CH:5]2

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67404638Tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-2-fluoroethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

生成物 1

HCID 57546100tert-Butyl 4-((1-(5-chloro-1H-indazol-7-yl)-2-fluoroethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate収率 86%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
55 °C

実験手順

Tert-butyl 4-((1-(5-chloro-2-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)-2-fluoroethoxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (420 mg, 0.660 mmol) was dissolved in TBAF (1M in THF) (8.5 mL, 8.50 mmol). The flask was sealed and heated at 55° C. for 1.5 h. The reaction was cooled to room temperature and diluted with ether, washed with water then brine, dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (30%-40% EtOAc/Hex) to give title compound (286 mg, 0.565 mmol, 86% yield) as a colorless oil. LC/MS (HPLC method 3): tR=3.78 min, 506.3(MH)+.

後処理

  1. customThe flask was sealed
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with water
  4. dry with materialbrine, dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography (30%-40% EtOAc/Hex)

出典と根拠

ORDレコード
ord-fad7a9f0192446759918fac2cd4b380a
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

読み込み中…