1-Propanol → 1-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

HRID 598029

反応式

HRID 598029 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][N:3]=1.[NH2:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][CH3:31])[N:24]([CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])[C:20]=2[C:19]2[N:18]=[CH:17][C:16](Br)=[CH:15][C:14]=2[N:13]=1.C(O)CC.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[NH2:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][CH3:31])[N:24]([CH2:25][C:26]([CH3:27])([OH:28])[CH3:29])[C:20]=2[C:19]2[N:18]=[CH:17][C:16]([C:5]3[CH:4]=[N:3][C:2]([F:1])=[CH:7][CH:6]=3)=[CH:15][C:14]=2[N:13]=1

参加物

8

反応物 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 2783397(6-Fluoropyridin-3-yl)boronic acidHCID 589706911-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol

生成物 1

HCID 589706971-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol収率 73.6%

試薬・触媒・溶媒 3

HCID 11776Triphenylphosphine触媒HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回

実験手順

2-Fluoropyridine-5-boronic acid (0.468 g, 3.32 mmol) was added to 1-(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol (1.1 g, 3.0 mmol) and 1-propanol (10 mL). The mixture was degassed and backfilled with nitrogen. Triphenylphosphine (23.8 mg, 0.0900 mmol), aqueous sodium carbonate (4.53 mL of 2 M), and water (2 mL) were added followed by palladium (II) acetate (6.8 mg, 0.030 mmol). The yellow suspension was heated at reflux for two hours. Water (20 mL) was added, and the 1-propanol was removed under reduced pressure. The remaining mixture was extracted with chloroform (2×100 mL). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was triturated with acetonitrile and isolated by filtration to provide 0.84 g of 1-[4-amino-2-ethyl-7-(6-fluoropyridin-3-yl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)-2-methylpropan-2-ol as a white powder, mp 250-251° C.

後処理

  1. customThe mixture was degassed
  2. temperatureThe yellow suspension was heated
  3. temperatureat reflux for two hours
  4. customthe 1-propanol was removed under reduced pressure
  5. extractionThe remaining mixture was extracted with chloroform (2×100 mL)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was triturated with acetonitrile
  11. customisolated by filtration

出典と根拠

ORDレコード
ord-a51a4eab74e545798ee940f8ed680196
出典データセット
uspto-grants-2011_03
特許番号
US07897609B2

関連ノート

読み込み中…