Potassium Carbonate → HCID 66656356, compound

HRID 1619674Notes

Reaction equation

HRID 1619674 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[C:10]([N+:20]([O-:22])=[O:21])=[N:11][N:12]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH:13]=2)[CH:3]=1.[C:23]([C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1)#[N:24].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].C([N+](CCCC)(CCCC)CCCC)CCC>C1C(/C(/C2[C-]=CC(Cl)=CC=2)=N\O)=CC=C(Cl)C=1.C1C(/C(/C2[C-]=CC(Cl)=CC=2)=N\O)=CC=C(Cl)C=1.[Cl-].[Cl-].[Pd+2].[Pd+2].CN(C=O)C>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([C:23]#[N:24])[CH:30]=2)=[CH:3][C:4]=1[C:9]1[C:10]([N+:20]([O-:22])=[O:21])=[N:11][N:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[CH:13]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 16028TetrabutylammoniumHCID 27343253-Cyanophenylboronic acidHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 594366304-chloro-2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]phenol

Product 1

HCID 66656356HCID 66656356, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 54751178287410-78-0CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

4-Chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenol (500 mg, 1.544 mmol), 3-cyanophenylboronic acid (453 mg, 3.09 mmol), di-mu-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl]palladium (II) dimer (63 mg, 0.0772 mmol), tri-tert-butylphosphonium tetrafluoroborate (45 mg, 0.154 mmol), potassium carbonate (426 mg, 3.09 mmol) and tetrabutyl ammonium hydroxyde solution (1M in MeOH, 0.31 mL, 0.31 mmol) were combined in a microwave vial. DMF (7.5 mL) was added and the vial was sealed. The mixture was heated at 130° C. for 1 hour under microwave irradiation and then partitioned between ethyl acetate (25 mL) and water (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage™ (10% to 80% EtOAc in heptane over 20 CV) to give the title compound (254 mg, 41%) as brown oil

Workup

  1. customthe vial was sealed
  2. custompartitioned between ethyl acetate (25 mL) and water (10 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (10 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on silica gel by Biotage™ (10% to 80% EtOAc in heptane over 20 CV)

Sources & evidence

ORD record
ord-0b5b7a1763fd46cd95fa363278e4b60a
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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