Triethylamine → 4-bromo-1-(tris(4-methoxyphenyl)methyl)-1H-pyrazole

HRID 56510

反応式

HRID 56510 の反応式
[Br:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.[CH3:7][O:8][C:9]1[CH:32]=[CH:31][C:12]([C:13](Cl)([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]([C:13]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:32][CH:31]=2)([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:6]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 163754-BromopyrazoleHCID 6305054,4',4''-Trimethoxytrityl chloride

生成物 1

HCID 584320664-bromo-1-(tris(4-methoxyphenyl)methyl)-1H-pyrazole収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 4-bromopyrazole (1.5 g, 10.2 mmol) and 4,4′,4″-trimethoxytrityl chloride (4.5 g, 12.2 mmol) in anhydrous DMF (20 mL) under argon was added triethylamine (3 mL, 21.5 mmol) and the mixture was cooled over an ice bath. After stirring for 10 min, the ice bath was removed and the reaction stirred for 2.5 hrs. The mixture was diluted with H2O and extracted with EtOAc. The combined organics were washed with H2O three times then saturated aqueous NaHCO3 and brine. The solution was dried over Na2SO4 and concentrated in vacuo. The crude oil was recrystallized from isopropanol to give 4-bromo-1-(tris(4-methoxyphenyl)methyl)-1H-pyrazole as off-white crystals (two batches; 2.55 g, 52% yield).

後処理

  1. temperaturethe mixture was cooled over an ice bath
  2. customthe ice bath was removed
  3. stirringthe reaction stirred for 2.5 hrs
  4. additionThe mixture was diluted with H2O
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with H2O three times
  7. dry with materialThe solution was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude oil was recrystallized from isopropanol

出典と根拠

ORDレコード
ord-e22b13b5bfdd44da9a4dce6762ee6bc5
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

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