Triethylborane → HCID 68209165, compound

HRID 2202813Notes

Reaction equation

HRID 2202813 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:22])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:29](B(CC)CC)[CH3:30].C1COCC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:22])([C:14]2[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([CH2:29][CH3:30])[N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 7357TriethylboraneHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 88888621HCID 88888621, compound

Product 1

HCID 68209165HCID 68209165, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Tetrakis-triphenylphosphine (0.083 g, 0.072 mmol) was added to a solution of 3,6-dichloro-4′-hydroxy-3′,4′,5′,6′-tetrahydro-2′H[2,4′]bipyridinyl-1′-carboxylic acid tert-butyl ester (0.25 g, 0.72 mmol) and potassium carbonate (0.2 g, 1.44 mmol) in DMF (4 mL). Triethylborane in THF (1 M, 0.79 mL, 0.79 mmol) was added via syringe under a nitrogen atmosphere and the reaction heated by microwave at 150° C. for 20 minutes. The reaction mixture was then cooled, filtered through celite and partitioned between DCM and water. The organics were separated, washed with 15% lithium chloride, dried over sodium sulphate, filtered and the solvent removed by evaporation under vacuum. The residue was purified by flash chromatography on silica eluting with 5-10% ethyl acetate/cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.086 g). LCMS m/z 241.3 [M+H]+. R.T.=5.20 min (Analytical Method 3).

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered through celite
  3. custompartitioned between DCM and water
  4. customThe organics were separated
  5. washwashed with 15% lithium chloride
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent removed by evaporation under vacuum
  9. customThe residue was purified by flash chromatography on silica eluting with 5-10% ethyl acetate/cyclohexane
  10. additionThe fractions containing the desired product
  11. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-d64b1baad5584a83ac2446bd81509dce
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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