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Potassium Hydroxide → HCID 11546710, 화합물

HRID 506787
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HRID 506787 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[N:13]([CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:12]=3)=[CH:10][C:3]=12.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([C:11]3[C:15]4=[N:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=[C:14]4[N:13]([CH2:24][CH2:25][N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)[CH:12]=3)=[CH:10][C:3]=12
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 46868294HCID 46868294, 화합물

생성물 1

HCID 11546710HCID 11546710, 화합물수율 64.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Treat bisazaindole 33 (40 mg, 0.067 mmol) with KOH at 3%/MeOH (10 mL) and reflux for 16 h. Concentrate the reaction medium under vacuum and divide the residue between EtOAc and saturated NaHCO3. The organic phase is washed with saturated NaHCO3, dried (Na2SO4) and submitted to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2) to give 34 (19.0 mg, 64.2%) as a white solid: 1H NMR (CDCl3) δ 10.94 (s broad, 1H), 8.07 (d, 1H, J=5.0 Hz), 7.62 (s, 1H), 7.14 (s, 1H), 7.05 (d, 1H, J=5.3 Hz), 6.66 (d, 1H, J=1.9 Hz), 4.23 (s overlapping t, 5H, J=6.4 Hz), 3.97 (s, 3H), 3.70 (t, 4H, J=4.6 Hz), 2.79 (t, 2H, J=6.4 Hz), 2.50 (t, 4H, J=4.6 Hz), TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.25, m/z obs.=442.1 (M+1).

후처리

  1. temperaturereflux for 16 h
  2. concentrationConcentrate the reaction medium under vacuum
  3. washThe organic phase is washed with saturated NaHCO3
  4. dry with materialdried (Na2SO4)

출처 및 근거

ORD 기록
ord-ffa2b833ce8d4a028bf2703a67af8d15
출처 데이터셋
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07786114B2

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