Triphenylmethane chloride → HCID 178450097、化合物

HRID 1432788ノート

反応式

HRID 1432788 の反応式
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]([CH3:13])[CH3:12])#[N:2].Br[C:18]1[S:22][C:21]([C:23]2[NH:27][N:26]=[N:25][N:24]=2)=[CH:20][CH:19]=1.[Cl-].C1(C(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C(=O)([O-])[O-].[Na+].[Na+].O.C(OCC)(=O)C>[CH2:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:18]2[S:22][C:21]([C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:20][CH:19]=2)=[CH:4][C:3]=1[C:1]#[N:2])[CH:11]([CH3:13])[CH3:12]

参加物

8

反応物 3

HCID 22260971Triphenylmethane chlorideHCID 54576546(3-Cyano-4-isobutoxyphenyl)boronic acidHCID 178419366HCID 178419366、化合物

生成物 1

HCID 178450097HCID 178450097、化合物収率 13.8%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

実験手順

In a mixed solution of 10 ml of 1,4-dioxane and 5 ml of a 1 M aqueous sodium carbonate solution were dissolved 0.31 g of (3-cyano-4-isobutoxyphenyl)boronic acid, 267 mg of 5-(5-bromo-2-thienyl)-1H-tetrazole, and 0.56 g of triphenylmethane chloride, and the solution was heated at 100° C. for 1.5 hours in the presence of 0.11 g of tetrakis-(triphenylphosphine)palladium. The reaction solution was diluted with water and ethyl acetate and then filtrated through celite. Conc. hydrochloric acid was added to the filtrate to make the solution pH=1, and the solution was stirred for 10 minutes. The solution was neutralized and extracted with a 1 M aqueous sodium hydroxide solution and the resulting aqueous layer was acidified with 1 M hydrochloric acid. Extraction with ethyl acetate was conducted and the resulting organic layer was washed with brine, followed by drying and concentration under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:THF:methanol:acetic acid=88.9:10:1:0.1) and then recrystallized from a mixed solvent (chloroform:THF:methanol:acetic acid=88.9:10:1:0.1) to obtain 52 mg of 2-isobutoxy-5-[5-(lH-tetrazol-5-yl)-2-thienyl]benzonitrile.

後処理

  1. filtrationfiltrated through celite
  2. additionConc. hydrochloric acid was added to the filtrate
  3. extractionextracted with a 1 M aqueous sodium hydroxide solution
  4. extractionExtraction with ethyl acetate
  5. washthe resulting organic layer was washed with brine
  6. customby drying
  7. concentrationconcentration under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:THF:methanol:acetic acid=88.9:10:1:0.1)
  9. customrecrystallized from a mixed solvent (chloroform:THF:methanol:acetic acid=88.9:10:1:0.1)

出典と根拠

ORDレコード
ord-65fa86b3865e4d25bd2c4ee842695afa
出典データセット
uspto-grants-2009_11
特許番号
US07612108B2

反応ノート

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