Sodium Carbonate → 5-(2,6-Difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

HRID 45888Notes

Reaction equation

HRID 45888 reaction equation
Br[C:2]1[C:7]([F:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][C:3]=1[F:12].[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[N:19]1[C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=[N:20]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:7]1[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=[C:3]([F:12])[C:2]=1[C:23]1[N:19]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[N:20]=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 137327452-Bromo-1,3-difluoro-4-nitrobenzene

Product 1

HCID 671850845-(2,6-Difluoro-3-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a solution of tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.04 mmol) in dimethoxyethane (30 mL), 2-bromo-1,3-difluoro-4-nitrobenzene (2.38 g, 10 mmol) in dimethoxyethane (20 mL) was added and the mixture was insufflated with nitrogen for 10 min. To the solution, 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (4 g, 15 mmol) in dimethoxyethane (30 mL) was added and the mixture was insufflated with nitrogen for 2 min, then 2 M sodium carbonate solution (40 mL) was added and the mixture was refluxed for 4 h. The mixture was cooled and the organic phase was concentrated to oil. By addition of diethyl ether a precipitate was obtained, filtered off and discarded. The filtrate was concentrated and purified by flash chromatography (eluant: dichloromethane/ethyl acetate 20:1). The title compound was obtained as oil (1.27 g, 40%).

Workup

  1. waitthe mixture was insufflated with nitrogen for 2 min
  2. temperaturethe mixture was refluxed for 4 h
  3. temperatureThe mixture was cooled
  4. concentrationthe organic phase was concentrated to oil
  5. additionBy addition of diethyl ether a precipitate
  6. customwas obtained
  7. filtrationfiltered off
  8. concentrationThe filtrate was concentrated
  9. custompurified by flash chromatography (eluant: dichloromethane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-d9eeec3776b94a95b5696dde8c7c0080
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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