Triethylamine → HCID 59868835, compound

HRID 1694546Notes

Reaction equation

HRID 1694546 reaction equation
Br[C:2]1[N:7]=[C:6]([C@@H:8]([OH:10])[CH3:9])[C:5]([F:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[H][H]>[Pd].C(Cl)Cl>[F:11][C:5]1[C:6]([C@@H:8]([OH:10])[CH3:9])=[N:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59868838HCID 59868838, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 59868835HCID 59868835, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

(1S)-1-(6-Bromo-3-fluoro-pyridin-2-yl)ethanol (1.3 g, 5.9 mmol), triethylamine (1.6 mL, 11.5 mmol) and palladium on carbon (0.64 g, 0.34 mmol) were mixed in DCM (25 mL). The flask was evacuated/filled with hydrogen gas in 4 cycles and then left at 2.5 atm pressure hydrogen gas at room temperature for 24 h. The mixture was filtered and the solid washed with DCM. The filtrate was washed with water and Brine and dried over sodium sulphate and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent DCM:methanol gradient) to yield 0.54 g (65% yield) of the title compound.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid washed with DCM
  3. washThe filtrate was washed with water and Brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (eluent DCM:methanol gradient)

Sources & evidence

ORD record
ord-513406045bee42238159ceb454208fc2
Source dataset
uspto-grants-2012_04
Patent number
US08158785B2

Reaction notes

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