Acetonitrile → tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

HRID 624070Notes

Reaction equation

HRID 624070 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[C:9]([NH:16][CH2:17][CH2:18]Br)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([O-])([O-])=O.[Cs+].[Cs+].CC#N>C(Cl)Cl>[C:12]([O:11][C:9](=[O:10])[NH:16][CH2:17][CH2:18][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 70984700tert-butyl (2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A flask was charged with 4-nitro-1H-pyrazole (3.5 g, 30.02 mmol), 2-(boc-amino)ethylbromide (6.9 g, 30.02 mmol), Cs2CO3 (1.07 g, 33.02 mmol) and MeCN (60 mL). The resulting reaction mixture was stirred at reflux (80° C.) for 1.5 h, then allowed to reach rt. The mixture was diluted with DCM, filtered, the filter cake was washed with DCM. The filtrate was concentrated to yield tert-butyl(2-(4-nitro-1H-pyrazol-1-yl)ethyl)carbamate as a light orange oil, which was used in the next step without further purification. LC-MS conditions B: tR=0.63 min, [M+H]+=257.35.

Workup

  1. customThe resulting reaction mixture
  2. customto reach rt
  3. filtrationfiltered
  4. washthe filter cake was washed with DCM
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-68558dc8d9c44c74889625296f773b75
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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