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Diisopropylamine → [5-(Benzyloxy)pyridin-2-yl](3-fluoropyridin-2-yl)methanone

HRID 573322
Notes
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Reaction equation

HRID 573322 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 677943-FluoropyridineHCID 860606535-(Benzyloxy)-N-methoxy-N-methylpyridine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 86688982[5-(Benzyloxy)pyridin-2-yl](3-fluoropyridin-2-yl)methanoneYield 52%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
3×
HCID 8058HexaneSolvent

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

  1. stirringThe mixture was stirred for 1 h
  2. stirringThe mixture was stirred at −78° C. for 2 h
  3. customThe mixture was quenched with saturated NH4Cl aqueous solution at −78° C.
  4. extractionextracted with AcOEt
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-38d53fbc7a51481ba818b101e7c17d22
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes