Dimethylformamide → HCID 68554418、化合物

HRID 2382131ノート

反応式

HRID 2382131 の反応式
[H-].[Na+].[CH:3]1([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][C:11]([F:15])=[CH:10][CH:9]=3)[CH2:5][CH2:4]1.C[N:17](C=O)C>>[CH:3]1([C:6]2[N:7]([NH2:17])[C:8]3[C:13]([CH:14]=2)=[CH:12][C:11]([F:15])=[CH:10][CH:9]=3)[CH2:5][CH2:4]1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 685530852-cyclopropyl-5-fluoro-1H-indole

生成物 1

HCID 68554418HCID 68554418、化合物収率 70%

反応条件

温度
0 °C

実験手順

A suspension of NaH (1.9 g, 47 mmol, 60% in mineral oil) in DMF (20 mL) at 0° C. is treated with 2-cyclopropyl-5-fluoro-1H-indole (550 mg, 3.14 mmol) and stirred at 0° C. for 1 h. The mixture is treated with HOSA (1.8 g, 15.7 mmol) portion wise and warmed to rt over 2 h. The mixture is then poured over ice, filtered through a pad of Celite, and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 5%-35% EtOAc in heptane to afford 2-cyclopropyl-5-fluoro-indol-1-ylamine (420 mg, 70%). MS: 191 (M+H); 1H NMR (300 MHz, CDCl3): δ 7.30 (m, 1H), 7.11 (m, 1H), 6.92 (m, 1H), 5.90 (s, 1H), 4.57 (s, NH2, 2H), 2.07 (m, 1H), 1.02 (m, 2H), 0.75 (m, 2H).

後処理

  1. additionThe mixture is treated with HOSA (1.8 g, 15.7 mmol) portion wise
  2. temperaturewarmed to rt over 2 h
  3. additionThe mixture is then poured over ice
  4. filtrationfiltered through a pad of Celite
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined organic layer is dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified by silica gel chromatography
  10. washeluting with 5%-35% EtOAc in heptane

出典と根拠

ORDレコード
ord-826dc192de9f4937bfc54fdda70a56f3
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

読み込み中…