Sodium methanethiolate → 6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(methylsulfanyl)-1,2-benzoxazole-5-carbaldehyde

HRID 577998Notes

Reaction equation

HRID 577998 reaction equation
Cl[C:2]1[C:6]2[CH:7]=[C:8]([CH:20]=[O:21])[C:9]([N:12]3[CH2:17][C@H:16]([CH3:18])[O:15][C@H:14]([CH3:19])[CH2:13]3)=[C:10]([F:11])[C:5]=2[O:4][N:3]=1.[CH3:22][S-:23].[Na+]>O1CCOCC1.O>[CH3:19][C@H:14]1[O:15][C@@H:16]([CH3:18])[CH2:17][N:12]([C:9]2[C:8]([CH:20]=[O:21])=[CH:7][C:6]3[C:2]([S:23][CH3:22])=[N:3][O:4][C:5]=3[C:10]=2[F:11])[CH2:13]1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 866581213-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde2×

Product 1

HCID 866581286-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-3-(methylsulfanyl)-1,2-benzoxazole-5-carbaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To an ice cold solution of 3-chloro-6-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-7-fluoro-1,2-benzoxazole-5-carbaldehyde (Intermediate 534, 0.3 g, 0.916 mmol) in dioxane was added sodium thiomethoxide (21% aq solution, 0.134 mL, 1.923 mmol) and stirred at room temperature for 12 hours. Reaction mixture was diluted with water and extracted with EtOAc (50 mL). Organic phase washed with brine (2×10 mL), dried over anhydrous sodium sulfate and, filtered, concentrated to give tilt product as white solid. Yield: 280 mg (90%).

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc (50 mL)
  3. washOrganic phase washed with brine (2×10 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give

Sources & evidence

ORD record
ord-fe165fcf94884bc283ae7fba39c3e4ec
Source dataset
uspto-grants-2015_05
Patent number
US09040528B2

Reaction notes

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