Acetonitrile → HCID 66738088, compound

HRID 561000Notes

Reaction equation

HRID 561000 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>ClCCl>[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 66738088HCID 66738088, compoundYield 99.7%

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, 19.40 mmol), morpholine (3.38 g, 38.80 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 hours and cool to room temperature. Dilute with dichloromethane and wash with water and saturated aqueous sodium chloride. Separate the organic layer from the aqueous layer and dry over magnesium sulfate. After filtration, concentrate in vacuo to give the crude title compound 6.23 g (99.7%). MS (ES) m/z 323 [M+1]+.

Workup

  1. customIn a flask, combine
  2. temperaturecool to room temperature
  3. washwash with water and saturated aqueous 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-7cb2e90f8ff7463083285bacc260a99a
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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