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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
ノート
印刷プレビュー

反応式

HRID 710328 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回
HCID 8857
Ethyl Acetate
溶媒
HCID 25517Ammonium Chloride溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-99ca6a4bac4b45a5807d474146d19cb3
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

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