Imidazole → 5-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

HRID 41511

反応式

HRID 41511 の反応式
CN(C)C=O.[OH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[CH:10]2.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>O>[Si:25]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[CH:10]2)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]

参加物

6

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1014381H-Indazol-5-ol

生成物 1

HCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

Charge a 10 L reaction vessel with N,N-dimethylformamide (DMF, 2.50 L), 5-hydroxyindazole (150.20 g, 1.12 mol) and 1H-imidazole (114.35 g, 1.68 mol). Cool the mixture to 0° C. and add tert-butyldimethylchlorosilane (253.16 g, 1.68 mol) over 0.5 hours. Stir the mixture at 18° C. for 3 hours. Add water (2.5 L) to the reaction slowly with an ice bath at 5° C. to maintain an internal temperature at around 20° C. Transfer the mixture to a separating funnel and extract with EA (2×2.5 L). Combine the extracts and wash with water (3×2.5 L) and brine. Dry the organic solutions over anhydrous sodium sulfate, filter, and evaporate to a red oil. Pass the oil through a silica gel pad and elute with eluent (0% to 30% EA in hexane) to afford the title compound as an orange oil which crystallizes. Yield: 300 g (100%). MS (ES) m/z 249 [M+1]+.

後処理

  1. additionCharge
  2. temperatureto maintain an internal temperature at around 20° C
  3. extractionTransfer the mixture to a separating funnel and extract with EA (2×2.5 L)
  4. washCombine the extracts and wash with water (3×2.5 L) and brine
  5. dry with materialDry the organic solutions over anhydrous sodium sulfate
  6. filtrationfilter
  7. customevaporate to a red oil
  8. washPass the oil through a silica gel pad and elute with eluent (0% to 30% EA in hexane)

出典と根拠

ORDレコード
ord-a2dfc5db6a0e49d685623b19671138b0
出典データセット
uspto-grants-2013_09
特許番号
US08530665B2

関連ノート

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