Hydrochloric Acid → HCID 57950448、化合物

HRID 930748ノート

反応式

HRID 930748 の反応式
Cl.[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][NH2:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Br[C:16]1[CH:24]=CC=C2[C:17]=1C(CCN)=CN2.[O-]S([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.C(O)CCC>[Br:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]3[CH2:12][CH2:13][NH:14][C:16]([CH3:24])([CH3:17])[C:8]=3[NH:9]2)=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24436Sodium SulfateHCID 180714Ethanamine, 2-(6-bromo-1H-indol-3-yl)-HCID 10944501HCID 10944501、化合物

生成物 1

HCID 57950448HCID 57950448、化合物収率 15%

試薬・触媒・溶媒 1

HCID 22056974HCID 22056974、化合物溶媒

反応条件

温度
60 °C

実験手順

Concentrated HCl (10 mL) was added to a suspension of a 2:1 mixture of 2-(6-bromo-1H-indol-3-yl)ethanamine and 2-(4-bromo-1H-indol-3-yl)ethanamine (9.90 g, 41.4 mmol) and Na2SO4 (30 g) in 1:1 acetone/n-butanol (100 mL). The resulting suspension was heated at 60° C. with stirring for 4 d. The suspension was cooled and concentrated under reduced pressure. The residue was diluted with EtOAc, and the suspension was filtered. The filtrate was washed with saturate NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (silica gel, (1:1 EtOAc/hexanes)/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH) 100:0 to 0:100) yielded the title compound (1.68 g, 15%) as a red foam: 1H NMR (500 MHz, CDCl3) δ 7.66 (br s, 1H), 7.45 (d, J=1.5 Hz, 1H), 7.32 (d, J=8.5 Hz, 1H), 7.19 (dd, J=8.5, 1.5 Hz, 1H), 3.20 (t, J=5.5 Hz, 2H), 2.68 (t, J=5.5 Hz, 2H), 1.47 (s, 6H).

後処理

  1. temperatureThe suspension was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with EtOAc
  4. filtrationthe suspension was filtered
  5. washThe filtrate was washed with saturate NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-1ed29bc7d1754d359e587d1f6351b8f0
出典データセット
uspto-grants-2016_03
特許番号
US09296743B2

反応ノート

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