4-Vinylpyridine → 1-(2-methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine

HRID 9449

반응식

HRID 9449 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C:6]3[N:13]=[CH:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]=3[C:4]=2[CH:3]=1.[CH:20]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)=[CH2:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][CH:17]([CH3:19])[CH2:16][N:15]1[C:5]2[C:4]3[CH:3]=[C:2]([CH:21]=[CH:20][C:22]4[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=4)[CH:11]=[CH:10][C:9]=3[N:8]=[C:7]([NH2:12])[C:6]=2[N:13]=[CH:14]1

참가 물질

7

반응물 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 111745978-bromo-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 688187741-(2-methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine수율 65.1%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

Nitrogen was bubbled through a solution of 8-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine (3.0 g, 9.4 mmol), 4-vinylpyridine (2.0 mL, 19 mmol), triphenylphosphine (246 mg, 0.94 mmol), and triethylamine (2.7 mL, 19 mmol) in acetonitrile (50 mL) for 15 minutes. Palladium (II) acetate (105 mg, 0.47 mmol) was added, and the reaction was heated at 100° C. for three days. The solvent was removed under reduced pressure, and the residue was adjusted to pH 2 with the addition of concentrated hydrochloric acid. Water was added, and the mixture was filtered through a layer of CELITE filter aid. Aqueous sodium carbonate (2 N) was added to the filtrate to adjust the solution to pH 10. The solution was then extracted with dichloromethane, and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:CMA in a gradient from 95:5 to 80:20) to provide 2.1 g of 1-(2-methylpropyl)-8-(2-pyridin-4-ylvinyl)-1H-imidazo[4,5-c]-quinolin-4-amine as a yellow solid.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was adjusted to pH 2 with the addition of concentrated hydrochloric acid
  3. additionWater was added
  4. filtrationthe mixture was filtered through a layer of CELITE
  5. filtrationfilter aid
  6. additionAqueous sodium carbonate (2 N) was added to the filtrate
  7. extractionThe solution was then extracted with dichloromethane
  8. dry with materialthe combined extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe crude product was purified by flash column chromatography on silica gel (
  12. washeluting with chloroform

출처 및 근거

ORD 기록
ord-06dcb0dc9288479ba77db93b0ebf51a7
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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