N-Iodosuccinimide → (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

HRID 589201ノート

反応式

HRID 589201 の反応式
[CH3:1][Si:2]([CH3:41])([CH3:40])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[C:8]1[N:13]2[N:14]=[CH:15][CH:16]=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1.C1C(=O)N([I:49])C(=O)C1>CC#N>[CH3:39][Si:36]([CH3:38])([CH3:37])[CH2:35][CH2:34][O:33][CH2:32][N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:40])[CH3:41])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([I:49])=[C:12]2[N:11]=[C:10]([C:17]2[CH2:18][C@@H:19]3[N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@H:22]([CH:23]=2)[CH2:21][CH2:20]3)[CH:9]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 67294324(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

生成物 1

HCID 67294877(1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (1R,5S)-tert-butyl 3-(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)pyrazolo[1,5-a]pyrimidin-5-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate (6.32 g, 10.5 mmol, preparation described previously) in CH3CN (50 mL) was added NIS (2.60 g, 11.5 mmol). The resulting solution was stirred at it for 1 h. The reaction quenched with Na2SO3 and CH3CN was evaporated. The aqueous residue was extracted with EtOAc, washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc) to afford the titled compound as a pale yellow oil (6.94 g).

後処理

  1. customThe reaction quenched with Na2SO3 and CH3CN
  2. customwas evaporated
  3. extractionThe aqueous residue was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by a SiO2 column (0-15% EtOAc/Hexanes, Rf=0.4 in 20% EtOAc)

出典と根拠

ORDレコード
ord-de0037525a214c42bd6ff39215c6a140
出典データセット
uspto-grants-2016_01
特許番号
US09227971B2

反応ノート

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