Sodium Carbonate → HCID 117770023, compound

HRID 1526324Notes

Reaction equation

HRID 1526324 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:19])[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[CH3:18])[CH:9]=[C:10](Br)[C:5]=2[NH:4][N:3]=1.CC1(C)C(C)(C)OB(B2OC(C)(C)C(C)(C)O2)O1.C([O-])(=O)C.[K+].I[C:44]1[CH:48]=[CH:47][N:46]([CH3:49])[N:45]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.CN(C)C=O>[NH2:1][C:2]1[C:6]2[C:7](=[O:19])[N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]3[CH3:18])[CH:9]=[C:10]([C:44]3[CH:48]=[CH:47][N:46]([CH3:49])[N:45]=3)[C:5]=2[NH:4][N:3]=1

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 133340573-Iodo-1-methyl-1H-pyrazoleHCID 117770272HCID 117770272, compound

Product 1

HCID 117770023HCID 117770023, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-amino-7-bromo-5-(2-methylcyclohexyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step G (200 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (861 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (22.0 mg), potassium acetate (121 mg) and N,N-dimethylformamide (3.0 mL) was heated with microwave irradiation at 110° C. for 5 hr. The reaction mixture was cooled to room temperature, and 3-iodo-1-methyl-1H-pyrazole (384 mg), aqueous sodium carbonate solution (2 M, 0.610 mL) and tetrakis(triphenylphosphine)palladium(0) (71.0 mg) were added thereto at room temperature. The reaction mixture was heated with microwave irradiation at 140° C. for 1 hr. The reaction mixture was cooled to room temperature, and poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/dichloromethane) to give the title compound (51.0 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customat room temperature
  3. temperatureThe reaction mixture was heated with microwave irradiation at 140° C. for 1 hr
  4. temperatureThe reaction mixture was cooled to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (methanol/dichloromethane)

Sources & evidence

ORD record
ord-7b2a72e7cada43ea99ea145062b7833f
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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