Potassium Carbonate → 2-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazine

HRID 407787Notes

Reaction equation

HRID 407787 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]([CH:9]([OH:11])[CH3:10])=[CH:7][C:6]([N:12]2[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]2[CH3:18])=[N:5]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:18][C:13]1[N:12]([C:6]2[CH:7]=[C:8]3[CH:9]([CH3:10])[O:11][CH2:2][CH2:3][N:4]3[N:5]=2)[C:16]([CH3:17])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866840491-(1-(2-Bromoethyl)-3-(2,5-dimethyl-1H-pyrrol-1-yl)-1H-pyrazol-5-yl)ethanol

Product 1

HCID 866840502-(2,5-Dimethyl-1H-pyrrol-1-yl)-4-methyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazineYield 37.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 100-mL round-bottomed flask equipped with a reflux condenser was charged with 150f (2.0 g, 1.0 eq., 6.4 mmol), K2CO3 (1.77 g, 2.0 eq., 12.8 mmol), acetonitrile (50 mL). The reaction mixture was reflux overnight. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 4:1 petroleum ether/ethyl acetate to afford 150g (550 mg, 37%, over two steps) as a colorless oil. MS-ESI: [M+H]+ 232.3

Workup

  1. customA 100-mL round-bottomed flask equipped with a reflux condenser
  2. temperatureThe reaction mixture was reflux overnight
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with 4:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-d88742f84ef641e98805f5eddd7dc8b9
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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