Potassium Carbonate → 7-isopropoxy-6-Methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)-1H-indole

HRID 218852

Reaction equation

HRID 218852 reaction equation
[CH:1]([O:4][C:5]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([C:20]#[C:21][CH3:22])[C:6]=1[NH:7][C:8](=O)[C:9](F)(F)F)([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:26]=C(I)[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].C([O-])([O-])=[O:37].[K+].[K+]>>[CH:1]([O:4][C:5]1[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]2[C:6]=1[NH:7][C:8]([CH3:9])=[C:20]2[C:21](=[O:37])[C:22]1[CH:26]=[C:25]([O:24][CH3:23])[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 2981335-Iodo-1,2,3-trimethoxybenzeneHCID 866376562-isopropoxy-3-methoxy-6-(prop-1-ynyl)-N-trifluoroacetylaniline

Product 1

HCID 672867187-isopropoxy-6-Methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)-1H-indoleYield 64%

Procedure

A mixture of the product of Step C (0.171 g; 0.54 mmol), 3,4,5-trimethoxyphenyl iodide (0.191 g; 0.65 mmol), Cl2Pd(PPh3)2 (0.044 g; 0.063 mmol); dry K2CO3 (0.23 g; 1.62 mmol in anhydrous DMF (5 ml) was degassed under reduced pressure and saturated with CO gas. The resulting mixture was vigorously stirred overnight at room temperature under CO balloon, then diluted to 50 ml with ethyl acetate and washed with water (3×15 ml), brine and dried over anhydrous MgSO4, filtered off and filtrate evaporated to dryness. The residue was purified by flash column chromatography (SiO2 CH2Cl2/ethyl acetate, 9:1) to give the title compound (0.143 g; 64% yield) as a yellow solid. 1H-NMR (CDCl3) 1.27 (d, 6H, J=6.14 Hz); 2.51 (s, 3H); 3.79 (s, 6H); 3.85 (s, 3H); 3.90 (s, 3H); 4.69 (m, 1H, J=6.14 Hz): 6.76 (d, 1H, J=8.75 Hz); 7.04 (s, 2H); 7.11 (d, 1H, J=8.75 Hz); 8.83 (broad m, 1H).

Workup

  1. custom1.62 mmol in anhydrous DMF (5 ml) was degassed under reduced pressure and saturated with CO gas
  2. additionballoon, then diluted to 50 ml with ethyl acetate
  3. washwashed with water (3×15 ml), brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered off
  6. customfiltrate evaporated to dryness
  7. customThe residue was purified by flash column chromatography (SiO2 CH2Cl2/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-1bd161adf2334851bd68e86ec6efacc3
Source dataset
uspto-grants-2012_06
Patent number
US08198466B2

Linked notes

Loading…