Water → HCID 57756227, compound

HRID 2361011Notes

Reaction equation

HRID 2361011 reaction equation
O.C([O-])(=O)C.[K+].[F:7][C:8]1[C:13](B(O)O)=[CH:12][CH:11]=[CH:10][N:9]=1.Cl[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=1>CC#N>[F:7][C:8]1[C:13]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 517044Potassium AcetateHCID 5818662-Amino-4-chloropyridineHCID 27832702-Fluoropyridine-3-boronic acid

Product 1

HCID 57756227HCID 57756227, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A pressure vessel was charged with 6.35 mL of water and degassed with nitrogen for 0.5 h. To this vessel was added potassium acetate (2.31 g, 23.5 mmol), 2-fluoropyridine-3-boronic acid (2.48 g, 17.6 mmol), 4-chloropyridin-2-amine (1.51 g, 11.7 mmol), dichloro-bis(di-tert-butylphenylphosphino)Pd(II) (0.146 g, 0.235 mmol) and 58.5 mL CH3CN. The mixture was purged under nitrogen for several additional minutes, and the pressure bottle was sealed. The reaction mixture was heated to 85° C. for 15 h. Upon cooling the layers were separated, and the organic portion was dried with Na2SO4 and concentrated. The resulting solid was triturated with ethyl acetate/diethyl ether to provide 4-(2-fluoropyridin-3-yl)pyridin-2-amine as a tan solid. MS m/z=190 [M+H]+. Calc'd for C10H8FN3: 189.19.

Workup

  1. customdegassed with nitrogen for 0.5 h
  2. customThe mixture was purged under nitrogen for several additional minutes
  3. customthe pressure bottle was sealed
  4. temperatureUpon cooling the layers
  5. customwere separated
  6. dry with materialthe organic portion was dried with Na2SO4
  7. concentrationconcentrated
  8. customThe resulting solid was triturated with ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-f6e8af724a2f43ecb9c64cab684b03b7
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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