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

HRID 710328Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-99ca6a4bac4b45a5807d474146d19cb3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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