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

HRID 1020500ノート

反応式

HRID 1020500 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cf6e10a0584146e486a705ff0a4289cc
出典データセット
uspto-grants-2014_05
特許番号
US08716335B2

反応ノート

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