Sodium Carbonate → 4-[2-(propan-2-yloxy)phenyl]-1H-imidazole

HRID 1039174ノート

反応式

HRID 1039174 の反応式
Br[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O)([CH3:9])[CH3:8].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[N:3]=[CH:4][NH:5][CH:6]=1)([CH3:9])[CH3:8]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 50840992-Isopropoxyphenylboronic acidHCID 178418934HCID 178418934、化合物

生成物 1

HCID 1784582854-[2-(propan-2-yloxy)phenyl]-1H-imidazole収率 73%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

Add tetrakis(triphenylphosphine)palladium(0) (500 mg) to a degassed suspension of 4-bromo-1H-imidazole (5.0 g, 34 mmol) and 2-isopropoxyphenyl boronic acid (9.19 g, 51 mmol) in dioxane (250 mL) and 2 M sodium carbonate solution (10.81 g, 102 mmol) at room temperature under nitrogen and heat the mixture at reflux for 21 hours. Remove the solvent under reduced pressure, dilute the residue with ethyl acetate (500 mL) and filter through a plug of Celite. Dry the filtrate over sodium sulfate, treat with silica gel (20 g) and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with ethyl acetate, to afford crude 4-(2-isopropoxyphenyl)-1H-imidazole (5.01 g, 73%) which is used without further purification in the next step.

後処理

  1. temperatureheat the mixture
  2. temperatureat reflux for 21 hours
  3. customRemove the solvent under reduced pressure
  4. additiondilute the residue with ethyl acetate (500 mL)
  5. filtrationfilter through a plug of Celite
  6. dry with materialDry the filtrate over sodium sulfate
  7. additiontreat with silica gel (20 g)
  8. customremove the solvent under reduced pressure
  9. customPurify the residue by flash column chromatography on silica gel
  10. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-78d7b18f24e74acaaca5681fb54259db
出典データセット
uspto-grants-2013_10
特許番号
US08552039B2

反応ノート

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