Sodium Carbonate → 1-(2-(tert-Butyldimethylsilyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)ethanone

HRID 710323Notes

Reaction equation

HRID 710323 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH:10][C:11](=[O:13])[CH3:12].[Si:14]([C:21]#[C:22][C:23]([C:25]1[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=1)=[O:24])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[Li+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[Si:14]([C:21]1[N:10]([C:11](=[O:13])[CH3:12])[C:3]2[C:2]([C:22]=1[C:23](=[O:24])[C:25]1[CH:26]=[C:27]([O:35][CH3:36])[C:28]([O:33][CH3:34])=[C:29]([O:31][CH3:32])[CH:30]=1)=[CH:7][CH:6]=[C:5]([O:8][CH3:9])[CH:4]=2)([C:17]([CH3:19])([CH3:18])[CH3:20])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 11403562N-(2-iodo-5-methoxyphenyl)acetamideHCID 247872403-(Tert-butyldimethylsilyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one

Product 1

HCID 667265851-(2-(tert-Butyldimethylsilyl)-6-methoxy-3-(3,4,5-trimethoxybenzoyl)-1H-indol-1-yl)ethanoneYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of N-(2-iodo-5-methoxyphenyl)acetamide (0.45 g; 1.55 mmol), 3-(tert-butyldimethylsilyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one (0.5 g; 1.51 mmol), LiCl (0.069 g; 1.6 mmol) and Na2CO3 (0.477 g; 4.5 mmol) in anhydrous DMF (8 ml) was degassed with N2 and temperature was raised to 100° C. with stirring. Pd(OAc)2 (0.15 g) was added and heating was continued for 1.5 h. The solvent was removed in vacuo and the residue was diluted to 100 ml with EtOAc. This was washed with H2O, dried over MgSO4, filtered and the filtrate was evaporated to dryness. The residue was purified by FCC (SiO2) to give the desired product (0.53 g; 69%) as creamy gum. 1H-NMR (CDCl3) 0.12 (s, 6H); 0.98 (s, 9H); 2.84 (s, 3H); 3.77 (s, 3H); 3.86 (s, 6H); 3.93 (s, 3H); 6.8 (dd, 1H, J=2.07, 8.73 Hz), 7.00 (d, 1H, J=8.73 Hz), 7.16 (broad s, 3H).

Workup

  1. customwas degassed with N2 and temperature
  2. additionPd(OAc)2 (0.15 g) was added
  3. temperatureheating
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted to 100 ml with EtOAc
  6. washThis was washed with H2O
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe filtrate was evaporated to dryness
  10. customThe residue was purified by FCC (SiO2)

Sources & evidence

ORD record
ord-07c710b26ed24e439a2bc17fc95dd6b2
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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