Diisopropylamine → HCID 57444582, compound
Reaction equation
C(NC(C)C)(C)C.CCCCCC.C([Li])CCC.[C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])(=[O:21])[CH3:20].[Br:27][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([CH:36]=1)[C:33](O)=[O:34].C1N=CN(C(N2C=NC=C2)=O)C=1>C1COCC1>[Br:27][C:28]1[CH:36]=[C:32]([C:33](=[O:34])[CH2:20][C:19]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:31]=[N:30][CH:29]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (5.41 g) in THF (30 mL) was added 1.5 M n-butyllithium hexane solution (35 mL) under dryice acetone cooling and the mixture was stirred at −78° C. for 10 minutes. To this was added tert-butyl acetate (5.87 g) under dryice acetone cooling and the mixture was stirred at −78° C. for 10 minutes and added dropwise to a solution of 5-bromonicotinic acid (3.00 g) and N,N-carbonyldiimidazole (2.65 g) in THF (30 mL) under dryice acetone cooling. The mixture was stirred at −78° C. for 0.5 hour. The mixture was partitioned between ethyl acetate and aq NH4Cl solution. The organic layer was separated, washed with aq NaHCO3 solution and brine, dried over MgSO4, and evaporated in vacuo. The residue was triturated with isopropyl ether to give tert-butyl 3-(5-bromo-3-pyridinyl)-3-oxopropanoate as a colorless powder (3.71 g).
Workup
- stirringthe mixture was stirred at −78° C. for 10 minutes
- stirringThe mixture was stirred at −78° C. for 0.5 hour
- customThe mixture was partitioned between ethyl acetate and aq NH4Cl solution
- customThe organic layer was separated
- washwashed with aq NaHCO3 solution and brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customThe residue was triturated with isopropyl ether
Sources & evidence
- ORD record
- ord-f751cd00a1b74dfa88b2e992f156ad23
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07317009B2
Reaction notes
Loading…