Potassium Carbonate → (3'-Methoxy-[4,4]bipyridinyl-3-yl)-methyl-amine

HRID 878051Notes

Reaction equation

HRID 878051 reaction equation
C[N:2]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1N1CCCCC1C)[C:3](=O)C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1.[CH3:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.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>[CH3:32][O:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][C:39]=1[C:24]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[NH:2][CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 467390193-Methoxypyridine-4-boronic acidHCID 86670691N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamide2×

Product 1

HCID 70663638(3'-Methoxy-[4,4]bipyridinyl-3-yl)-methyl-amine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (4-bromo-pyridin-3-yl)-methyl-amine (50 mg, 0.267 mmol, example 25, intermediate b) and 3-methoxypyridine-4-boronic acid (CAS RN 1008506-24-8) (61.35 mg, 0.4 mmol) in dry DMF (3 mL) in a sealed tube was added potassium carbonate (2.14 mmol) and the reaction mixture was purged with argon for 10 min. Then, Pd(PPh3)4 (30.89 mg, 0.03 mmol) was added and again purged with nitrogen for 15 min. The reaction mixture was heated at 100° C. for 16 hours. After cooling to room temperature the reaction mixture was filtered through a bed of celite and the filter cake washed with EtOAc. The solvent was evaporated, the residue was dissolved in EtOAc and washed with water. The organic layer was dried over sodium sulphate and evaporated to get compound that was used in next step without further purification. Brown solid (55 mg, 95%). MS (ESI): m/z=216.2 [M+H]+.

Workup

  1. customthe reaction mixture was purged with argon for 10 min
  2. customagain purged with nitrogen for 15 min
  3. temperatureAfter cooling to room temperature the reaction mixture
  4. filtrationwas filtered through a bed of celite
  5. washthe filter cake washed with EtOAc
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in EtOAc
  8. washwashed with water
  9. dry with materialThe organic layer was dried over sodium sulphate
  10. customevaporated
  11. customto get compound that
  12. customwas used in next step without further purification

Sources & evidence

ORD record
ord-0c0efd976bc64f48909b87bf871c39e7
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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