Trityl chloride → (R)-tert-butyl 3-(3-(3-bromo-1-trityl-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

HRID 1465699ノート

反応式

HRID 1465699 の反応式
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16]([C@@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)[NH:15][N:14]=3)[CH:11]=2)[NH:6][N:5]=1.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]3[N:17]=[C:16]([C@@H:18]4[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]4)[NH:15][N:14]=3)[CH:11]=2)[N:6]([C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[N:5]=1

参加物

5

反応物 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 178451955HCID 178451955、化合物

生成物 1

HCID 86695578(R)-tert-butyl 3-(3-(3-bromo-1-trityl-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Added Sodium Hydride (100 mg; 2.5 mmol) to a solution of (R)-tert-butyl 3-(3-(3-bromo-1H-indazol-5-yl)-1H-1,2,4-triazol-5-yl)piperidine-1-carboxylate (530 mg, 0.988 mmol) in DMF (5 ml) at 0° C., then stirred for 30 minutes. Trityl Chloride (570 mg, 2.05 mmol) was added, and stirred at room temperature overnight. Added water (100 ml), filtered precipitated solid, washed with water, dried, then chromatographed on silica gel eluting with 30% v/v EtOAc/Hexanes to yield a mixture of mono and dialkylated products (560 mg, 8:2 mono/dialkylation).

後処理

  1. stirringstirred at room temperature overnight
  2. filtrationAdded water (100 ml), filtered
  3. customprecipitated solid
  4. washwashed with water
  5. customdried
  6. customchromatographed on silica gel eluting with 30% v/v EtOAc/Hexanes
  7. customto yield
  8. additiona mixture of mono and

出典と根拠

ORDレコード
ord-2a0424c0ea7443a197beef34032ad632
出典データセット
uspto-grants-2015_04
特許番号
US08999966B2

反応ノート

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