Water → 6-Thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

HRID 12284

反応式

HRID 12284 の反応式
Cl[C:2]1[CH:3]=[C:4]([C:17]2[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:20]3[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=3[N:18]=2)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[N:7]=1.[S:34]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35]1.C(=O)([O-])[O-].[K+].[K+].O>C(COC)OC>[S:34]1[CH:38]=[CH:37][C:36]([C:2]2[CH:3]=[C:4]([C:17]3[N:21]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:27])[CH3:28])[C:20]4[CH:30]=[CH:31][CH:32]=[CH:33][C:19]=4[N:18]=3)[C:5](=[O:16])[N:6]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:13])([CH3:14])[CH3:15])[N:7]=2)=[CH:35]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 581760Thiophene-3-boronic acidHCID 686802706-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

生成物 1

HCID 686802276-Thiophen-3-yl-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

44 mg of 6-chloro-2-(2-trimethylsilanylethoxymethyl)-4-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-2H-pyridazin-3-one, 14 mg of thiophene-3-boronic acid and 36 mg of potassium carbonate are dissolved 1.5 ml of a 1:2 mixture of water and dimethoxyethane, and argon is passed through the solution for degassing. Addition of 7 mg of (1,1′-bis(diphenylphosphine) -ferrocene)palladium(II) chloride-dichloromethane complex is followed by stirring at 85° C. for 4 hours. For workup, it is diluted with water and extracted several times with ethyl acetate. The combined organic phases are dried using a silica gel cartridge, and the solvent is distilled off. The crude product is purified by silica gel chromatography (n-heptane/ethyl acetate).

後処理

  1. customfor degassing
  2. additionAddition of 7 mg of (1,1′-bis(diphenylphosphine) -ferrocene)palladium(II) chloride-dichloromethane complex
  3. additionFor workup, it is diluted with water
  4. extractionextracted several times with ethyl acetate
  5. customThe combined organic phases are dried
  6. distillationthe solvent is distilled off
  7. customThe crude product is purified by silica gel chromatography (n-heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-89db74143efc4aeca5ac7a1cab291567
出典データセット
uspto-grants-2010_06
特許番号
US07727989B2

関連ノート

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