Nitrogen → HCID 58486414, 화합물

HRID 1890760노트

반응식

HRID 1890760 반응식
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

참가 물질

6

반응물 4

HCID 947NitrogenHCID 25953Cesium fluorideHCID 2856454-Fluorophenylboronic acidHCID 58486430HCID 58486430, 화합물

생성물 1

HCID 58486414HCID 58486414, 화합물수율 87%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5288860a365843d2b32deea83aad87cc
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507490B2

반응 노트

불러오는 중…