Hydrochloric Acid → HCID 57950448, 화합물

HRID 930748노트

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HRID 930748 반응식
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

참가 물질

6

반응물 4

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

생성물 1

HCID 57950448HCID 57950448, 화합물수율 15%

시약·촉매·용매 1

HCID 22056974HCID 22056974, 화합물용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1ed29bc7d1754d359e587d1f6351b8f0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296743B2

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