2-Chloro-5,6,7,8-tetrahydroquinolin-5-one → 2-hydroxy-3-(5-oxo-7,8-dihydro-6H-quinolin-2-yl)-1H-indole-5-carbonitrile
Reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[O:13]=[C:14]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:23]#[N:24])[CH:20]=2)[NH:15]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1>[OH:13][C:14]1[NH:15][C:16]2[C:21]([C:22]=1[C:2]1[CH:11]=[CH:10][C:9]3[C:8](=[O:12])[CH2:7][CH2:6][CH2:5][C:4]=3[N:3]=1)=[CH:20][C:19]([C:23]#[N:24])=[CH:18][CH:17]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 2-chloro-7,8-dihydroquinolin-5(6H)-one (50 mg, 0.275 mmol) and 2-oxoindoline-5-carbonitrile (45.7 mg, 0.289 mmol) in tetrahydrofuran (1.4 mL) was added a 1.0 M solution of sodium bis(trimethylsilyl)amide (641 μL, 0.641 mmol). The mixture was stirred for 3 min at RT and then heated in a microwave oven to 110° C. for 10 min. After cooling to RT the reaction was quenched by addition of methanol (1 mL). The resulting solution was evaporated to dryness. The crude was purified by flash chromatography (silica gel, dichloromethane/methanol) yielding an orange solid. Amount 17 mg. Yield 20%.
Workup
- temperatureheated in a microwave oven to 110° C. for 10 min
- temperatureAfter cooling to RT the reaction
- customwas quenched by addition of methanol (1 mL)
- customThe resulting solution was evaporated to dryness
- customThe crude was purified by flash chromatography (silica gel, dichloromethane/methanol)
- customyielding an orange solid
Sources & evidence
- ORD record
- ord-900c4be5b5824114af92fe04c4026bf9
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266855B2
Reaction notes
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