Diisopropylamine → [5-(Benzyloxy)pyridin-2-yl](3-fluoropyridin-2-yl)methanone
Reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[F:13][C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34](N(OC)C)=[O:35])=[N:32][CH:33]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.CCCCCC>[CH2:20]([O:27][C:28]1[CH:29]=[CH:30][C:31]([C:34]([C:15]2[C:14]([F:13])=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:35])=[N:32][CH:33]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (2.08 g) in THF (50 mL) was added 1.6 M n-BuLi in hexane (12.3 mL) at −5° C. The mixture was stirred for 15 min. The mixture was cooled to −78° C., and a solution of 3-fluoropyridine (1.74 g) in THF (10 mL) was added. The mixture was stirred for 1 h. To the mixture was added a solution of 5-(benzyloxy)-N-methoxy-N-methylpicolinamide (4.87 g) in THF (5 mL). The mixture was stirred at −78° C. for 2 h. The mixture was quenched with saturated NH4Cl aqueous solution at −78° C. and extracted with AcOEt. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.87 g).
Workup
- stirringThe mixture was stirred for 1 h
- stirringThe mixture was stirred at −78° C. for 2 h
- customThe mixture was quenched with saturated NH4Cl aqueous solution at −78° C.
- extractionextracted with AcOEt
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
Sources & evidence
- ORD record
- ord-38d53fbc7a51481ba818b101e7c17d22
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029536B2
Reaction notes
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