Acetonitrile → 4-(6-Fluoro-4-iodo-pyridin-3-ylmethyl)-morpholine

HRID 1640888Notes

Reaction equation

HRID 1640888 reaction equation
Br[CH2:2][C:3]1[C:4]([I:10])=[CH:5][C:6]([F:9])=[N:7][CH:8]=1.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CC#N.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[F:9][C:6]1[N:7]=[CH:8][C:3]([CH2:2][N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[C:4]([I:10])[CH:5]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 66674459HCID 66674459, compound

Product 1

HCID 667380884-(6-Fluoro-4-iodo-pyridin-3-ylmethyl)-morpholineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
81 °C

Procedure

In a flask, combine 5-bromomethyl-2-fluoro-4-iodo-pyridine (6.13 g, 19.4 mmol), morpholine (3.38 g, 38.8 mmol) and dry CH3CN (100 mL) under nitrogen. Add N,N-diisopropylethylamine (6.76 mL, 38.80 mmol, 2 M THF solution). Heat at 81° C. for 2 h and cool to RT. Dilute with DCM and wash with water and aqueous saturated sodium chloride. Separate the organic layer from the aqueous layer and dry over magnesium sulfate. After filtration, concentrate in vacuo to give the title compound 6.23 g (100%). MS (ES) m/z 323 [M+1]+.

Workup

  1. customIn a flask, combine
  2. temperaturecool to RT
  3. washwash with water and aqueous saturated sodium chloride
  4. customSeparate the organic layer from the aqueous layer
  5. dry with materialdry over magnesium sulfate
  6. filtrationAfter filtration
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-8ffd83b6008a47fdad87ca6d6f151195
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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