2-Bromopyridine → HCID 117770726, compound

HRID 1526297Notes

Reaction equation

HRID 1526297 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:19])[N:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C: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+].Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][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]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH:9]=[C:10]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)[C:5]=2[NH:4][N:3]=1

Participants

9

Reactant 5

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 117770411HCID 117770411, compound

Product 1

HCID 117770726HCID 117770726, compoundYield 11.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-amino-7-bromo-5-(2-methylphenyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one obtained in Step F of Example 1 (130 mg), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (114 mg), (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) (14.9 mg), potassium acetate (80.0 mg) and N,N-dimethylformamide (2.0 mL) was heated with microwave irradiation at 110° C. for 7 hr. The reaction mixture was cooled to room temperature, and 2-bromopyridine (111 mg), aqueous sodium carbonate solution (2 M, 0.350 mL) and tetrakis(triphenylphosphine)palladium(0) (40.4 mg) were added thereto. The reaction mixture was heated with microwave irradiation at 140° C. for 1 hr. The reaction mixture was cooled to room temperature, water was added thereto, 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 thin layer silica gel chromatography (methanol/dichloromethane) to give the title compound (15.0 mg).

Workup

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

Sources & evidence

ORD record
ord-81217e5b14214d0e9a6dafcac7ffc62b
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…