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

HRID 919085

Reaction equation

HRID 919085 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-42ab1a38aafa4a9999ebc7f8487eebf0
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Linked notes

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