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

HRID 710323노트

반응식

HRID 710323 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-07c710b26ed24e439a2bc17fc95dd6b2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

반응 노트

불러오는 중…