Sodium hydride → 6-Bromo-1,2-dihydro-2-(4-trifluoromethylphenyl)-1-(2-trimethylsilyl ethoxymethyl)-3H-indazol-3-one
Reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:23])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[NH:10]2)=[CH:6][CH:5]=1.[CH3:24][Si:25]([CH2:28][CH2:29][O:30][CH2:31]Cl)([CH3:27])[CH3:26]>C1COCC1>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8](=[O:23])[N:9]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:17][CH:18]=3)[N:10]2[CH2:31][O:30][CH2:29][CH2:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of NaH in mineral oil (60%, 0.17 g, 0.0041 mol) was added portionwise to a solution of the product of Step 4 (1.3 g, 0.0035 mol) in dry THF (50 mL) at room temperature under N2. After 20 min, SEM chloride (0.68 g, 0.0041 mol) in THF (15 mL) was added and the resulting slurry stirred at room temperature overnight. The mixture was quenched with brine (10 mL) and extracted into ether (3×20 mL). The organic phase was washed with 1N HCl (10 mL), 2N NaOH (10 mL), brine (10 mL), dried (MgSO4) and concentrated to give crude product as an oil.
Workup
- customThe mixture was quenched with brine (10 mL)
- extractionextracted into ether (3×20 mL)
- washThe organic phase was washed with 1N HCl (10 mL), 2N NaOH (10 mL), brine (10 mL)
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customto give crude product as an oil
Sources & evidence
- ORD record
- ord-0bc31f18fb3c4f20972f94acb25f5c8a
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449585B2
Reaction notes
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