Nitrogen → N1-Benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

HRID 2093362노트

반응식

HRID 2093362 반응식
N#N.[CH2:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]1[N:15]=[N:16][C:17](Cl)=[C:18]([CH3:21])[C:19]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.[F-].[Cs+]>O1CCOCC1>[CH2:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]1[N:15]=[N:16][C:17]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)=[C:18]([CH3:21])[C:19]=1[CH3:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 947NitrogenHCID 25953Cesium fluorideHCID 2856454-Fluorophenylboronic acidHCID 86655911N1-Benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

생성물 1

HCID 67320023N1-Benzyl-N2-(6-(4-fluorophenyl)-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

Treat a N2 degassed mixture of N1-benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine (6.40 g, 22.0 mmol), 4-fluorophenylboronic acid (9.24 g, 66.0 mmol) and CsF (10.0 g, 66.0 mmol) in 1,4-dioxane (220 mL) with (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) chloride (2.70 g, 3.30 mmol). Heat the reaction mixture at 95° C. overnight. Cool, and partition between saturated NaHCO3 (aq) and EtOAc. Separate the layers, and extract the aqueous layer with EtOAc. Combine the organic layers, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue by flash silica gel chromatography (gradient of 0 to 6% 2M NH3/MeOH in CH2Cl2) to afford the title compound as a waxy solid (4.91 g, 64%). ES/MS m/z 351.2 (M+1).

후처리

  1. customdegassed
  2. temperatureCool
  3. custompartition between saturated NaHCO3 (aq) and EtOAc
  4. customSeparate the layers
  5. extractionextract the aqueous layer with EtOAc
  6. dry with materialdry over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate under reduced pressure
  9. customPurify the residue by flash silica gel chromatography (gradient of 0 to 6% 2M NH3/MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-3a4377fc7b5341cfb00f9c15ece34c03
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445493B2

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