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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
Notes
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Reaction equation

HRID 710328 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 6228Dimethylformamide
Solvent
2×
HCID 8857Ethyl AcetateSolvent
HCID 25517Ammonium ChlorideSolvent

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

  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)

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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes