Nitrogen → HCID 58486414、化合物

HRID 1890760ノート

反応式

HRID 1890760 の反応式
N#N.Cl[C:4]1[N:9]=[N:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]2)=[C:6]([CH3:25])[C:5]=1[CH3:26].[F:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.[F-].[Cs+]>O1CCOCC1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:4]2[N:9]=[N:8][C:7]([N:10]3[CH2:15][CH2:14][CH:13]([N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:12][CH2:11]3)=[C:6]([CH3:25])[C:5]=2[CH3:26])=[CH:30][CH:29]=1

参加物

6

反応物 4

HCID 947NitrogenHCID 25953Cesium fluorideHCID 2856454-Fluorophenylboronic acidHCID 58486430HCID 58486430、化合物

生成物 1

HCID 58486414HCID 58486414、化合物収率 87%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

Treat a N2 degassed mixture of tert-butyl 1-(6-chloro-4,5-dimethylpyridazin-3-yl)piperidin-4-yl(methyl)carbamate (3.01 g, 8.48 mmol), 4-fluorophenylboronic acid (1.23 g, 8.80 mmol) and CsF (4.08 g, 26.8 mmol) in 1,4-dioxane (80 mL) with (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (1.10 g, 1.35 mmol). Heat the resulting mixture under N2 at 95° C. overnight. Partition the reaction mixture between H2O and EtOAc. Separate the layers, and wash the organic layer with brine. Dry the organic layer over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 20 to 80% EtOAc in hexanes) to provide the title compound (3.05 g, 87%). ES/MS m/z 415.2 (M+1).

後処理

  1. customdegassed
  2. customPartition the reaction mixture between H2O and EtOAc
  3. customSeparate the layers
  4. washwash the organic layer with brine
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by flash silica gel chromatography (gradient of 20 to 80% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-5288860a365843d2b32deea83aad87cc
出典データセット
uspto-grants-2013_08
特許番号
US08507490B2

反応ノート

読み込み中…