Pyridine → HCID 67171662, compound

HRID 1506459Notes

Reaction equation

HRID 1506459 reaction equation
[F:1][C:2]1[CH:30]=[C:29]2[C:5]([CH2:6][CH2:7][CH:8]3[C:12](O)([C:13]4[O:17][N:16]=[C:15]([C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=5)[C:14]=4[C:24]([F:27])([F:26])[F:25])[O:11][N:10]=[C:9]32)=[CH:4][C:3]=1[C:31]([O:33][CH3:34])=[O:32].N1C=CC=CC=1.S(Cl)(Cl)=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:30]=[C:29]2[C:5]([CH2:6][CH2:7][C:8]3[C:9]2=[N:10][O:11][C:12]=3[C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:14]=2[C:24]([F:27])([F:26])[F:25])=[CH:4][C:3]=1[C:31]([O:33][CH3:34])=[O:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67171102HCID 67171102, compound

Product 1

HCID 67171662HCID 67171662, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred suspension of methyl 8-fluoro-3-hydroxy-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3,3a,4,5-tetrahydronaphtho[1,2-c]isoxazole-7-carboxylate (Preparation 67B, 0.055 g, 0.115 mmol) in anhydrous toluene (1.0 mL) at room temperature was added pyridine (0.2 mL) followed by thionyl chloride (0.014 mL, 0.196 mmol). The reaction mixture was stirred at room temperature for 15 min. and then at 80° C. for 15 min. The reaction mixture was cooled to room temperature and concentrated. The solid residue was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The dichloromethane extract was collected and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded methyl 8-fluoro-3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carboxylate [0.050 g, 0.109 mmol, 94%] as an off white solid product. The product had an HPLC ret. time=3.28 min. (condition B). LC/MS M+1=459.1.

Workup

  1. waitat 80° C. for 15 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated
  4. customThe solid residue was partitioned between dichloromethane
  5. extractionThe dichloromethane extract
  6. customwas collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-bdc49639a8bb4e9483239acfae7fd5d6
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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