Hydrochloric Acid → 2,2,2-trichloro-1-(6-chloro-5-(4-ethoxyphenyl)-1H-indol-3-yl)ethanone

HRID 1054647ノート

反応式

HRID 1054647 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=1.N1C=CC=CC=1.[Cl:26][C:27]([Cl:32])([Cl:31])[C:28](Cl)=[O:29].Cl>C1COCC1>[Cl:26][C:27]([Cl:32])([Cl:31])[C:28]([C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH3:19])=[CH:13][CH:12]=3)[CH:4]=2)[NH:8][CH:7]=1)=[O:29]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6420Trichloroacetyl chlorideHCID 866986496-Chloro-5-(4-ethoxyphenyl)-1H-indole

生成物 1

HCID 866986512,2,2-trichloro-1-(6-chloro-5-(4-ethoxyphenyl)-1H-indol-3-yl)ethanone収率 9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 6-chloro-5-(4-ethoxyphenyl)-1H-indole (500.0 mg, 1.84 mmol) in anhydrous THF (5 mL) was added pyridine (436.0 mg, 5.52 mmol) and trichloroacetyl chloride (10 mL) at 0° C. under N2. The reaction mixture was stirred at room temperature under N2 for 12 hours. The mixture was poured into 0.5 N HCl (200 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (9-25% EtOAc/petroleum ether:EtOAc) to give the title compound (70.0 mg, 9%) as a green solid. 1H NMR (400 MHz, CDCl3) δ 8.80 (br, 1 H), 8.40 (s, 1 H), 8.36 (d, J=3.2 Hz, 1 H), 7.59 (s, 1 H), 7.42 (d, 2H), 6.97 (d, 2 H), 4.12 (q, J=7.00 Hz, 2 H), 1.45 (t, J=7.00 Hz, 3 H).

後処理

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic layers were washed with brine (100 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (9-25% EtOAc/petroleum ether:EtOAc)

出典と根拠

ORDレコード
ord-42ce0111987e44a28091af437bc21fb9
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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