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

HRID 919085

반응식

HRID 919085 반응식
[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]

참가 물질

6

반응물 4

HCID 6386tert-Butanol2회HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 6736864-Bromo-1-methyl-1H-pyrazole-5-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-42ab1a38aafa4a9999ebc7f8487eebf0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09272990B2

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