Sodium Carbonate → 4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 595850Notes

Reaction equation

HRID 595850 reaction equation
Br[C:2]1[C:3]([F:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:10][N:11]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[N:12]1.C([O-])([O-])=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>COCCOC>[F:9][C:3]1[C:2]([C:14]2[CH:13]=[N:12][N:11]([CH3:10])[CH:15]=2)=[CH:7][N:6]=[C:5]([NH2:8])[CH:4]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 579174075-Bromo-4-fluoropyridin-2-amine

Product 1

HCID 1180463264-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amineYield 75.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To the reaction mixture of 5-bromo-4-fluoropyridin-2-amine (369 mg, 1.932 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (603 mg, 2.90 mmol), PdCl2(dppf)DCM (141 mg, 0.193 mmol) and DME (9.660 μL), 2M Na2CO3 (3.220 mL) was added. The reaction mixture was heated at microwave synthesizer (120° C., 12 min). To the reaction mixture, anhydrous sodium sulfate was added, filtered, and concentrated. The crude product was purified by flash chromatography eluting with 0-100% EtOAc (containing 10% of MeOH/heptane to provide 280 mg of desired product in 75% yield. LCMS (m/z): 193.1 (MH+), 0.35 min.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 0-100% EtOAc (
  6. additioncontaining 10% of MeOH/heptane

Sources & evidence

ORD record
ord-87b5327baa2849cdb19181ed34b9d597
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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