Potassium Carbonate → 2-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinoline

HRID 2404994

반응식

HRID 2404994 반응식
[N+](=[C:3](P(=O)(OCC)OCC)C(=O)C)=[N-].[CH2:15]([C:17]1[N:18]([CH2:30][CH2:31][CH2:32][CH:33]=O)[C:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:29]=1)[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:15]([C:17]1[N:18]([CH2:30][CH2:31][CH2:32][C:33]#[CH:3])[C:19]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N:22]=[CH:21][C:20]=2[N:29]=1)[CH3:16]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 866266434-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanalHCID 136104435(1Z)-1-diazo-1-diethoxyphosphorylpropan-2-one

생성물 1

HCID 866266442-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinoline수율 80.1%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Diethyl 1-diazo-2-oxopropylphosphonate (9.6 g, 1.2 eq.) was added to a solution of 4-(2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal (11.15 g, 41.7 mmol, 1 eq.) and potassium carbonate (11.6 g, 2 eq.) in methanol. The reaction mixture was stirred until analysis by TLC indicated that all of the starting material had been consumed. The reaction mixture was filtered and the filter cake was rinsed until clear. The filtrate was concentrated under reduced pressure to provide crude product as an oil. The oil was partitioned between dichloromethane (200 mL) and water (100 mL). The organic layer was washed sequentially with water and brine (2×100 mL) and then concentrated under reduced pressure to provide 8.8 g of 2-ethyl-1-(4-pentynyl)-1H-imidazo[4,5-c]quinoline.

후처리

  1. customhad been consumed
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was rinsed until clear
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto provide crude product as an oil
  6. customThe oil was partitioned between dichloromethane (200 mL) and water (100 mL)
  7. washThe organic layer was washed sequentially with water and brine (2×100 mL)
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c4e14c44a98c40d18569bb08db4ce8ae
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802853B2

연결된 노트

불러오는 중…