Ethyl acetate hexane → HCID 23086738, compound
Reaction equation
O=C1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[N:6][C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)=[CH:4][C:3]1=2.C[Mg]Cl.[CH3:25]CCCCC.C([O:34][CH2:35][CH3:36])(=O)C>O1CCCC1>[CH3:25][C:35]1([OH:34])[CH2:36][CH:10]([CH3:11])[CH2:9][C:8]2[N:7]=[N:6][C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[CH:13]=3)=[CH:4][C:3]1=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
5-Oxo-3-(3-trifluoromethylphenyl)-7,8-dihydro-6H-cinnoline (200 mg, 0.65 mmol) obtained in Example 66 was dissolved in tetrahydrofuran (1 mL) and cooled to −20° C., followed by adding a tetrahydrofuran solution (0.26 mL, 0.78 mmol) of 3N methylmagnesium chloride to the reaction liquid and reacting for 3 hours while elevating temperature. To the reaction liquid was added distilled water (1 mL) to quench, followed by adding ethyl acetate (5 mL) and a 1N aqueous solution of sodium hydrogen sulfate (5 mL) for extraction, washing an organic layer with a saturated saline solution (3 ml), drying with sodium sulfate anhydride and purification of residue obtained by concentration using silica gel column chromatography (hexane/ethyl acetate=2/1 to 1/1) to obtain an objective compound (74.1 mg, 35%) as pale yellow crystal.
Workup
- customto the reaction liquid
- customTo the reaction liquid
- additionwas added
- distillationdistilled water (1 mL)
- customto quench
- additionby adding ethyl acetate (5 mL)
- extractiona 1N aqueous solution of sodium hydrogen sulfate (5 mL) for extraction
- washwashing an organic layer with a saturated saline solution (3 ml)
- dry with materialdrying with sodium sulfate anhydride and purification of residue
- customobtained by concentration
Sources & evidence
- ORD record
- ord-72415712be9b47ee90e2523271009fd0
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563893B2
Reaction notes
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