3-Bromopyridine → HCID 86725312, compound
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li]CCCC.[CH2:13]([O:15][C:16]([N:18]1[CH2:33][CH2:32][C:22]2[C:23]3[C:24](=[O:31])[CH2:25][CH2:26][C:27]=3[C:28]([I:30])=[CH:29][C:21]=2[CH2:20][CH2:19]1)=[O:17])[CH3:14]>C1COCC1>[CH2:13]([O:15][C:16]([N:18]1[CH2:33][CH2:32][C:22]2[C:23]3[C:24]([OH:31])([C:2]4[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=4)[CH2:25][CH2:26][C:27]=3[C:28]([I:30])=[CH:29][C:21]=2[CH2:20][CH2:19]1)=[O:17])[CH3:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a stirred solution of 3-bromopyridine (0.11 ml, 1.13 mmol) in THF (5 ml) under Ar at −78° C., n-BuLi (2.5 M in hexane, 0.45 ml, 1.13 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, followed by dropwise addition of Intermediate 1 (0.15 g, 0.38 mmol) in THF (5 ml). The mixture was stirred for 2 h at −78° C., allowed to warm to room temperature, and quenched by slow addition of aqueous saturated NH4Cl (50 ml). The mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the sub-title compound as tan oil that was used without further purification. MS: ESI (positive): 479 (M+1).
Workup
- stirringThe mixture was stirred for 2 h at −78° C.
- temperatureto warm to room temperature
- customquenched by slow addition of aqueous saturated NH4Cl (50 ml)
- extractionThe mixture was extracted with EtOAc (3×)
- washThe combined EtOAc extracts were washed with brine
- dry with materialdried (Na2SO4), and solvent
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6216cd49c0ca48af9d361e96ea0c0934
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284277B2
Reaction notes
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