Triethylamine → 1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine

HRID 1818214

반응식

HRID 1818214 반응식
[CH2:1](N(CC)CC)[CH3:2].C([B-](F)(F)F)=C.[K+].Br[C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[N:29]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:28]([CH2:34][CH2:35][CH3:36])=[N:27][C:21]=3[C:22]([NH2:26])=[N:23][C:24]=2[CH:25]=1.[OH-].[Na+]>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O>[CH3:32][CH:31]([CH3:33])[CH2:30][N:29]1[C:20]2[C:19]3[CH:18]=[CH:17][C:16]([CH:1]=[CH2:2])=[CH:25][C:24]=3[N:23]=[C:22]([NH2:26])[C:21]=2[N:27]=[C:28]1[CH2:34][CH2:35][CH3:36]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 219842607-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amineHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 219844201-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매HCID 10311-Propanol용매

실험 절차

Triethylamine (3.0 equivalents), potassium vinyltrifluoroborate (1.0 equivalent) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (0.2 equivalent) were added to a solution of 7-bromo-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.0 equivalent) in n-propanol (30 ml/g). The reaction mixture was heated at reflux under a nitrogen atmosphere until it was complete (between four and 18 hours) and then poured into water (3 volumes). The pH of the mixture was monitored and adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide if needed. The mixture was extracted with ethyl acetate, and the combined organic fractions were filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile to provide 1-(2-methylpropyl)-2-propyl-7-vinyl-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere until it
  3. custom(between four and 18 hours)
  4. extractionThe mixture was extracted with ethyl acetate
  5. filtrationthe combined organic fractions were filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography on silica gel (
  8. washeluting with chloroform
  9. custommethanol in a gradient from 100:0 to 90:10), followed by recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-26b75d503f0d4382b06cc48cf8cad176
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598382B2

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