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

HRID 56510

반응식

HRID 56510 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e22b13b5bfdd44da9a4dce6762ee6bc5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434707B2

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