2-Vinylpyridine → (E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9503

反応式

HRID 9503 の反応式
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[CH:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)=[CH2:31].Br[C:39]1[CH:40]=[CH:41][C:42]2[C:43]3[N:52]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:51]([CH2:58][O:59][CH2:60][CH3:61])=[N:50][C:44]=3[C:45]([NH2:49])=[N:46][C:47]=2[CH:48]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH2:60]([O:59][CH2:58][C:51]1[N:52]([CH2:53][CH2:54][CH2:55][O:56][CH3:57])[C:43]2[C:42]3[CH:41]=[CH:40][C:39](/[CH:31]=[CH:30]/[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=4)=[CH:48][C:47]=3[N:46]=[C:45]([NH2:49])[C:44]=2[N:50]=1)[CH3:61]

参加物

7

反応物 4

HCID 75212-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 219840707-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 21984053(E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

A thick walled glass tube, equipped with magnetic stir-bar, was charged with toluene (20 mL/g), palladium (II) acetate (0.1 equivalents), tri-ortho-tolylphosphine (0.3 equivalents), triethylamine (3.0 equivalents), 2-vinylpyridine (1.0 equivalent), and 7-bromo-2-ethoxymethyl-1-(3-methoxypropyl)-1H-imidazo[4,5-c]quinolin-4-amine (1.0 eq.). The tube was purged with nitrogen and sealed. The reaction mixture was heated at 120° C. for 24–48 hours. The reaction mixture was allowed to cool and then concentrated under reduced pressure. The solid residue was partitioned between dichloromethane and water, and the mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide. The organic layer was separated and purified by flash chromatography on silica gel (eluting with chloroform:methanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile to provide (E)-2-ethoxymethyl-1-(3-methoxypropyl)-7-(2-pyridin-2-ylvinyl)-1H-imidazo[4,5-c]quinolin-4-amine as an off-white solid.

後処理

  1. customA thick walled glass tube, equipped with magnetic stir-bar
  2. customThe tube was purged with nitrogen
  3. customsealed
  4. temperatureto cool
  5. concentrationconcentrated under reduced pressure
  6. customThe solid residue was partitioned between dichloromethane and water
  7. additionthe mixture was adjusted to pH 12 with the addition of 10% aqueous sodium hydroxide
  8. customThe organic layer was separated
  9. custompurified by flash chromatography on silica gel (
  10. washeluting with chloroform
  11. custommethanol in a gradient from 100:0 to 90:10) followed by recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-02f3772b166949dc9620d2ef20591eba
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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