Hydrochloric Acid → HCID 89524760, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[C:13]([C:15]1([CH:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]2)[CH2:18][CH2:17][CH2:16]1)#N.Cl.C([O-])(O)=[O:33].[Na+]>CCOCC>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:13]([C:15]1([CH:19]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]2)[CH2:18][CH2:17][CH2:16]1)=[O:33]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-bromopyridine (410 mg, 2.6 mmol) in ether (10 mL) was added 2.5M n-BuLi (1.04 mL, 2.6 mmol) dropwise and the solution was stirred at −78° C. for 45 minutes. Then a solution of Example 265C (500 mg, 2.0 mmol) in ether (2 mL) was added to the solution at −78° C. and the mixture was stirred for 2 hours. 1N HCl aqueous solution was added to the mixture till pH<7 and the resulting solution was stirred at room temperature for 1 hour. The reaction mixture was basified with aqueous solution of NaHCO3 and the solution was extracted with EtOAc (20 mL×3). The combined organic phases were washed with brine (30 mL), dried over Na2SO4, filtered, and concentrated to obtain the title compound (140 mg, 21% yield) as a yellow oil. MS: m/z 275 (M−55).
Workup
- stirringthe mixture was stirred for 2 hours
- stirringthe resulting solution was stirred at room temperature for 1 hour
- extractionthe solution was extracted with EtOAc (20 mL×3)
- washThe combined organic phases were washed with brine (30 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a7fabdd10dfc4c708a88fe296b1f672d
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772500B2
Reaction notes
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