Sodium Carbonate → 4-(4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)morpholin-3-one

HRID 2206237Notes

Reaction equation

HRID 2206237 reaction equation
FC(F)(F)S(O[C:7]1[C:11]2[C:12]([O:16][CH3:17])=[N:13][CH:14]=[CH:15][C:10]=2[N:9]([C:18]2[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=2[F:25])[N:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:36]2[CH:41]=[CH:40][C:39]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][C:43]3=[O:48])=[CH:38][CH:37]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O>[F:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([F:25])[C:18]=1[N:9]1[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:16][CH3:17])[C:11]=2[C:7]([C:36]2[CH:37]=[CH:38][C:39]([N:42]3[CH2:47][CH2:46][O:45][CH2:44][C:43]3=[O:48])=[CH:40][CH:41]=2)=[N:8]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 692342734-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholin-3-oneHCID 117987899HCID 117987899, compound

Product 1

HCID 1179880524-(4-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)phenyl)morpholin-3-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl trifluoromethanesulfonate (150 mg) obtained in Step C of Example 35, 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholin-3-one (145 mg) and sodium carbonate (78 mg) in DME/water (1.5 mL/0.070 mL) was added dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) (21 mg) under nitrogen atmosphere. The reaction mixture was stirred under microwave irradiation at 120° C. for 1 hr. The insoluble substance was removed by the filtration, the filtrate was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography (ethyl acetate/petroleum ether) to give the title compound (143 mg).

Workup

  1. customThe insoluble substance was removed by the filtration
  2. additionthe filtrate was added to water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by thin layer silica gel chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-3b9db79c5709437d958414ff2c4320f1
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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