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

HRID 2093362ノート

反応式

HRID 2093362 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

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 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).

後処理

  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)

出典と根拠

ORDレコード
ord-3a4377fc7b5341cfb00f9c15ece34c03
出典データセット
uspto-grants-2013_05
特許番号
US08445493B2

反応ノート

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