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Potassium Carbonate → (1-(3-(4-Iodophenyl)prop-2-ynyl)-6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 710328
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HRID 710328 반응식
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:33][C:34]#[C:35][C:36]1[CH:41]=[CH:40][C:39]([I:42])=[CH:38][CH:37]=1>CN(C=O)C.[NH4+].[Cl-].CCOC(C)=O>[I:42][C:39]1[CH:40]=[CH:41][C:36]([C:35]#[C:34][CH2:33][N:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[C:7]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=[O:13])=[CH:8]2)=[CH:37][CH:38]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 10359957Bpr-0L075HCID 667264161-(3-Bromoprop-1-ynyl)-4-iodobenzene

생성물 1

HCID 66726594(1-(3-(4-Iodophenyl)prop-2-ynyl)-6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone수율 32%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매2회
HCID 8857
Ethyl Acetate
용매
HCID 25517Ammonium Chloride용매

반응 조건

온도
50 °C

실험 절차

To a stirred suspension of (6-methoxy-1H-indol-3-yl)(3,4,5-trimethoxyphenyl)methanone (0.69 g, 0.5 mmol) and K2CO3 in anhydrous DMF (2 ml) was added the solution of 1-(3-bromoprop-1-ynyl)-4-iodobenzene (0.150 g, 0.47 mmol) in anhydrous DMF (0.5 ml) and the resulting mixture was stirred at 50° C. for 2 h, diluted with saturated solution of NH4Cl (5 ml) and diluted to 30 ml with EtOAc. The organic layer was washed with H2O and dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2), to give the desired product (0.079 g; 32%), as light yellow paste. 1H-NMR (CDCl3) 3.84 (s, 6H); 3.89 (s, 3H); 3.91 (s, 3H); 5.06 (s, 2H); 6.94 (d, 1H, J=2.06 Hz); 7.00 (dd, 1H, J=2.22, 7.1 (s, 2H); 8.75 Hz); 7.1 (d, 2H, J=8.27 Hz); 7.65 (d, 2H, J=8.42 Hz); 7.72 (s, 1H); 8.25 (d, 1H, J=8.78 Hz).

후처리

  1. washThe organic layer was washed with H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by FCC (SiO2)

출처 및 근거

ORD 기록
ord-99ca6a4bac4b45a5807d474146d19cb3
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09181182B2

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