Tetrahydrofuran → 1H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-

HRID 557224ノート

反応式

HRID 557224 の反応式
C([Li])(C)(C)C.C(OC([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.[O:23]1CCC[CH2:24]1>>[F:22][C:19]1[C:20]([CH:24]=[O:23])=[C:21]2[C:16]([CH2:15][CH2:14][NH:13]2)=[CH:17][CH:18]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 17985580Tert-butyl 6-fluoroindoline-1-carboxylateHCID 178418306HCID 178418306、化合物

生成物 1

HCID 179858381H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-収率 42%

実験手順

Add tert-butyllithium (21.13 ml, 35.93 mmol, 1.7 M solution in heptane) to a solution of 1-(tert-butoxycarbonyl)-2,3-dihydro-6-fluoroindole (3.28 g, 13.82 mmol) in anhydrous tetrahydrofuran (100 ml) at −78 C. Stir for 20 minutes, quench with excess dimethylformamide, and stir for 1 hour at −78 C. Warm to room temperature, add saturated aqueous ammonium chloride, and extract with ethyl acetate. Concentrate the combined organic phases under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound as a bright yellow solid (0.91 g, 42%).

後処理

  1. customquench with excess dimethylformamide
  2. stirringstir for 1 hour at −78 C
  3. additionadd saturated aqueous ammonium chloride
  4. extractionextract with ethyl acetate
  5. concentrationConcentrate the combined organic phases under reduced pressure

出典と根拠

ORDレコード
ord-d6497d076ccd403bba13a0007ac9ae9f
出典データセット
uspto-grants-2011_11
特許番号
US08058425B2

反応ノート

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