Diisopropylamine → 6-(2-(4-chlorophenyl)-1,3-dioxolan-2-yl)-4-(3-methoxyphenyl)-1-methyl-1,8-naphthyridin-2(1H)-one
Reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[Li+].CC([N-]C(C)C)C.[C:21]([O:25]C(C)=O)(C)(C)[CH3:22].[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([C:41]3[CH:42]=[C:43]([C:49]([C:51]4[CH:56]=[CH:55][CH:54]=[C:53]([O:57][CH3:58])[CH:52]=4)=O)[C:44]([NH:47][CH3:48])=[N:45][CH:46]=3)[O:40][CH2:39][CH2:38][O:37]2)=[CH:32][CH:31]=1>C1COCC1>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2([C:41]3[CH:42]=[C:43]4[C:44](=[N:45][CH:46]=3)[N:47]([CH3:48])[C:21](=[O:25])[CH:22]=[C:49]4[C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([O:57][CH3:58])[CH:52]=3)[O:40][CH2:39][CH2:38][O:37]2)=[CH:32][CH:31]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of diisopropylamine (1.32 mL, 9.43 mmol) in THF, a solution of BuLi (7.86 mL, 7.08 mmol, 0.9 M solution in hexane) was added at −20° C. and the resulting mixture was stirred for 30 min. To this solution of LDA was added tBuOAc (0.95 mL, 7.08 mmol) at −78° C. The mixture was stirred for 30 min and a solution compound G (500 mg, 1.18 mmol) was added to it. The reaction mixture was allowed to warm to RT and stirred overnight. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with EtOAc (50 mL). The organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by column chromatography to obtain 0.3 g (57%) of compound H off-white solid.
Workup
- stirringThe mixture was stirred for 30 min
- stirringstirred overnight
- customThe reaction mixture was quenched with saturated ammonium chloride solution
- extractionextracted with EtOAc (50 mL)
- dry with materialThe organic layer was dried (Na2SO4)
- filtrationfiltered
- customevaporated
- customThe crude product was purified by column chromatography
Sources & evidence
- ORD record
- ord-85e4739cb20b4e57955282dc1a1403b9
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343996B2
Reaction notes
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