tert-Butanol → tert-butyl N-(4-bromo-1-methyl-1H-pyrazol-5-yl)carbamate

HRID 919085

反応式

HRID 919085 の反応式
[Br:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1C(O)=O.C([N:13]([CH2:16]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:25])C=CC=CC=1.[C:35]([OH:39])([CH3:38])([CH3:37])[CH3:36]>C1(C)C=CC=CC=1>[C:35]([O:39][C:16](=[O:25])[NH:13][C:3]1[N:4]([CH3:7])[N:5]=[CH:6][C:2]=1[Br:1])([CH3:38])([CH3:37])[CH3:36]

参加物

6

反応物 4

HCID 6386tert-Butanol2 回HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6736864-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 67957972tert-butyl N-(4-bromo-1-methyl-1H-pyrazol-5-yl)carbamate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

4-Bromo-2-methyl-2H-pyrazole-3-carboxylic acid (2 g, 9.76 mmol) and triethylamine (1.50 mL, 10.73 mmol) were combined in toluene (10 mL). Diphenylphosphoryl azide (2.31 mL, 10.73 mmol) was added and the reaction stirred at room temperature for 3 hours. tert-Butanol (1.12 mL, 11.71 mmol) was added and the reaction was stirred at 60° C. overnight. After cooling the t-BuOH was removed under vacuum and the reaction was submitted to EtOAc/H2O workup. The crude material was purified via silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

後処理

  1. stirringthe reaction was stirred at 60° C. overnight
  2. customwas removed under vacuum
  3. customThe crude material was purified via silica gel chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-42ab1a38aafa4a9999ebc7f8487eebf0
出典データセット
uspto-grants-2016_03
特許番号
US09272990B2

関連ノート

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