1-Bromo-3-methylbutane → HCID 66847207, compound

HRID 1466595Notes

Reaction equation

HRID 1466595 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].Br[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C(OCC)(=O)C>[CH2:10]([N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1)[CH2:11][CH:12]([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazole

Product 1

HCID 66847207HCID 66847207, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 4-Nitro-1H-pyrazole (234 mg, 2.06 mmol, 1.0 eq), 1-Bromo-3-methylbutane (0.30 ml, 2.48 mmol, 1.2 eq), and Cesium carbonate (1.01 g, 3.10 mmol, 1.5 eq) in 5.0 mL 1,2-Dimethoxyethane was stirred at 55° C. for 12 hours. The reaction mixture was cooled to room temperature and diluted with 25 mL ethyl acetate and filtered. The filtrate was then concentrated and the residue was dissolved in 5 mL dichloromethane and purified by flash column chromatography (silica, 0-80% ethyl acetate in heptane in 30 minutes) to yield 357.6 mg (94.32%) of Isopentyl-4-nitro-1H-pyrazole as a white solid. LCMS (ESI) m+H=184.1 1H NMR (400 MHz, CDCl3) δ 8.11 (s, 1H), 8.06 (s, 1H), 4.20-4.14 (m, 2H), 1.80 (dd, J=14.8, 7.1, 2H), 1.60 (dp, J=13.4, 6.7, 1H), 0.97 (d, J=6.6, 6H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was then concentrated
  4. dissolutionthe residue was dissolved in 5 mL dichloromethane
  5. custompurified by flash column chromatography (silica, 0-80% ethyl acetate in heptane in 30 minutes)

Sources & evidence

ORD record
ord-988102e95e4a40bab7244e1fff4cf51b
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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