Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-formyl-1H-indole-6-carboxylate → Methyl 1-(5-(5-ethyl-2-fluorophenyl)pyrimidin-2-yl)-3-(1-hydroxyethyl)-1H-indole-6-carboxylate
Reaction equation
[CH3:1][Mg]Br.[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([F:33])=[C:10]([C:12]2[CH:13]=[N:14][C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=4)[C:20]([CH:31]=[O:32])=[CH:19]3)=[N:16][CH:17]=2)[CH:11]=1)[CH3:5]>C1COCC1>[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]([F:33])=[C:10]([C:12]2[CH:17]=[N:16][C:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([C:27]([O:29][CH3:30])=[O:28])[CH:25]=4)[C:20]([CH:31]([OH:32])[CH3:1])=[CH:19]3)=[N:14][CH:13]=2)[CH:11]=1)[CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methylmagnesium bromide (3 M in ether, 0.45 mL, 1.33 mmol) was added at 0° C. to a solution of 331c) (0.36 g, 0.89 mmol) in THF (70 mL) and the resulting mixture was stirred at this temperature for 6 h. The mixture was quenched with ammonium chloride solution (20 mL) and extracted with ethyl acetate (2×50 mL). The organic phase was washed with brine, dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography [silica; dichloromethane with 0-1.5% methanol]. Light yellow solid. Yield: 0.22 g (59% of theory)
Workup
- customThe mixture was quenched with ammonium chloride solution (20 mL)
- extractionextracted with ethyl acetate (2×50 mL)
- washThe organic phase was washed with brine
- dry with materialdried over sodium sulfate
- customevaporated
- customThe residue was purified by flash column chromatography [silica; dichloromethane with 0-1.5% methanol]
Sources & evidence
- ORD record
- ord-ad173cff4bdf46d888a5b25a3f6ba913
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315490B2
Reaction notes
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