Triethylsilane → 4-Chloroindoline

HRID 544915ノート

反応式

HRID 544915 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2

参加物

4

反応物 2

HCID 12052TriethylsilaneHCID 913454-Chloroindole

生成物 1

HCID 30163064-Chloroindoline収率 90.5%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

A solution of 4-chloroindole (3.15 g) and triethylsilane (8.30 ml) in trifluoroacetic acid (32 ml) was stirred at 50° C. for 30 minutes. The solvent was evaporated under reduced pressure, and the residue was basified with a saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate twice, and the combined organic layer was dried over magnesium sulfate. The insoluble materials were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20) to give the titled compound (2.89 g) as colorless oil. APCI-Mass m/Z 154/156 (M+H). 1H-NMR (DMSO-d6) δ 2.94 (t, J=8.7 Hz, 2H), 3.46 (t, J=8.7 Hz, 2H), 5.83 (s, 1H), 6.40 (d, J=7.7 Hz, 1H), 6.50 (d, J=8.0 Hz, 1H), 6.90 (t, J=7.9 Hz, 1H).

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe mixture was extracted with ethyl acetate twice
  3. dry with materialthe combined organic layer was dried over magnesium sulfate
  4. filtrationThe insoluble materials were filtered off
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0-80:20)

出典と根拠

ORDレコード
ord-7f7bc41dae8a4570a930edacd3540cd5
出典データセット
uspto-grants-2011_05
特許番号
US07935674B2

反応ノート

読み込み中…