Water → 4-[1-(6-Bromopyridin-2-yl)-2-fluoroethyl]morpholine

HRID 385998Notes

Reaction equation

HRID 385998 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8](Br)[CH2:9][F:10])[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH:8]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8083Morpholine2×HCID 81531Diisopropylethylamine2×HCID 595262542-Bromo-6-(1-bromo-2-fluoroethyl)pyridine

Product 1

HCID 595261924-[1-(6-Bromopyridin-2-yl)-2-fluoroethyl]morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-6-(1-bromo-2-fluoroethyl)pyridine (70 mg, 0.25 mmol), morpholine (0.022 mL, 0.25 mmol) and DIPEA (0.048 mL, 0.27 mmol) were stirred in DMF (1 mL) at room temperature for 4 hours. Additional morpholine (10.78 μL, 0.12 mmol) and DIPEA (0.024 mL, 0.14 mmol) were added and the resulting solution stirred at room temperature overnight. Water was added and the reaction mixture was extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification of the residue by silica gel column chromatography (6-50% EtOAc-hexanes) gave the title compound as a pale yellow oil.

Workup

  1. extractionthe reaction mixture was extracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by silica gel column chromatography (6-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4f6bf62e0a944177b3b0a9192a4bfa16
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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