Dimethylformamide → HCID 117770092, compound

HRID 1526364Notes

Reaction equation

HRID 1526364 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](=[O:21])[N:8]([C:12]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])[CH:9]=[C:10](Br)[C:5]=2[NH:4][N:3]=1.[CH3:22][N:23]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[N:24]1.C(=O)([O-])[O-].[Na+].[Na+].CN(C)C=O>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>[NH2:1][C:2]1[C:6]2[C:7](=[O:21])[N:8]([C:12]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])[CH:9]=[C:10]([C:25]3[CH:26]=[CH:27][N:23]([CH3:22])[N:24]=3)[C:5]=2[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 27600771-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 117770314HCID 117770314, compound

Product 1

HCID 117770092HCID 117770092, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-(3-amino-7-bromo-4-oxo-1,4-dihydro-5H-pyrazolo[4,3-c]pyridin-5-yl)-3-fluorobenzonitrile obtained in Step G (160 mg), 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (191 mg), tetrakis(triphenylphosphine)palladium(0) (53 mg), aqueous sodium carbonate solution (2 M, 0.460 mL) and N,N-dimethylformamide (10 mL) was heated with microwave irradiation at 130° C. for 90 min under argon atmosphere. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (basic silica gel, methanol/ethyl acetate) to give a crude product. The crude product was crystallized from ethyl acetate/diethyl ether to give the title compound (44 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (basic silica gel, methanol/ethyl acetate)
  6. customto give a crude product
  7. customThe crude product was crystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-367f7a6fbbbd47d4bd8426b9d3dc4a66
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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