Acetic Acid → HCID 18537078、化合物

HRID 2298628ノート

反応式

HRID 2298628 の反応式
[C:1]([C:5]1[CH:9]=[C:8](C(Cl)=O)[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Si](C=[N+]=[N-])(C)C.[BrH:27].[C:28]([OH:31])(=O)[CH3:29]>C(#N)C>[C:1]([C:5]1[CH:9]=[C:8]([C:28](=[O:31])[CH2:29][Br:27])[N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 167693TrimethylsilyldiazomethaneHCID 27993221-benzyl-3-tert-butyl-1H-pyrazole-5-carbonyl chloride

生成物 1

HCID 18537078HCID 18537078、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of 1 g (3.6 mmol) of 3-(tert-butyl)-1-benzylpyrazole-5-carbonyl chloride (Maybridge, Cornwall, UK) was dissolved in dry acetonitrile (4 mL) and 4.5 mL (9 mmol) of 2 M trimethylsilyldiazomethane in hexanes (Aldrich, Milwaukee, Wis., USA) was added. After stirring 1 h 20 min at room temperature, the mixture was cooled on an ice bath for 5 min. To this, 30% hydrogen bromide in acetic acid (2 mL, 10 mmol) was added dropwise over 15 min. This was stirred an additional 15 minutes on an ice bath. Filtration of the precipitated solid and evaporation of the solvents gave 1-[3-(tert-butyl)-1-benzylpyrazol-5-yl]-2-bromoethan-1-one (1.47 g, quantitive yield) as an orange solid. 1H-NMR (DMSO-d6; 300 MHz) δ7.33-7.06 (m, 5H), 7.08 (s, 1H), 5.64 (s, 2H), 4.57 (s, 2H), 1.28 (s, 9H). Mass spectrum (MALDI-TOF, CHCA matrix, m/z): Calcd. for C16H19N2OBr, 335.1 and 337.1 (M+H), found 335.6 and 337.6.

後処理

  1. temperaturethe mixture was cooled on an ice bath for 5 min
  2. stirringThis was stirred an additional 15 minutes on an ice bath
  3. filtrationFiltration of the precipitated solid and evaporation of the solvents

出典と根拠

ORDレコード
ord-65807bceb76d4aefa509376736f0a9a5
出典データセット
uspto-grants-2002_12
特許番号
US06492403B1

反応ノート

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