Methyl iodide → HCID 86658133, compound

HRID 245541Notes

Reaction equation

HRID 245541 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH:19]=[O:20])=[CH:17][C:12]3[C:13]([OH:16])=[N:14][O:15][C:11]=3[C:10]=2[F:21])[CH2:3]1.[C:22]([O-])([O-])=O.[K+].[K+].CI>C(#N)C>[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[C:18]([CH:19]=[O:20])=[CH:17][C:12]3[C:13]([O:16][CH3:22])=[N:14][O:15][C:11]=3[C:10]=2[F:21])[CH2:3]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178461507HCID 178461507, compound2×

Product 1

HCID 86658133HCID 86658133, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-hydroxy-1,2-benzisoxazole-5-carbaldehyde (Intermediate 556, 0.15 g, 0.5 mmol) in acetonitrile was added K2CO3 (0.08 g, 0.6 mmol) followed by MeI (0.07 mL, 0.5 mmol). The reaction mixture was stirred at 60° C. for 2 hours. The reaction mixture was concentrated, washed with water and extracted with EtOAc (2×10 mL). The organic layer was dried over Na2SO4, filtered and concentrated to provide the title product, along with a by-product, 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-2-methyl-3-oxo-2,3-dihydro-1,2-benzoxazole-5-carbaldehyde. The mixture was used in the next step with out further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with water
  3. extractionextracted with EtOAc (2×10 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5712c91ef4fb4d728383db34083a3e4f
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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