Ammonium Chloride → [4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

HRID 573340Notes

Reaction equation

[F:1][C:2]1[C:3]([C:9](N(OC)C)=[O:10])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([Mg]Br)=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[NH4+].[Cl-]>C1COCC1>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([C:9]([C:3]2[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][N:4]=2)=[O:10])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of 3,5-difluoro-N-methoxy-N-methylpyridine-2-carboxamide (2.5 g) in THF (50 mL) was added [4-(benzyloxy)phenyl](bromo)magnesium (1 M solution in THF, 12.3 mL) at −78° C. The mixture was stirred at −78° C. for 3 h, treated with saturated NH4Cl aqueous solution and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane). The product was crystallized from AcOEt/hexane to give the title compound (2.3 g).

Workup

extractionextracted with AcOEt
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (AcOEt/hexane)
customThe product was crystallized from AcOEt/hexane

Sources & evidence

ORD record: ord-d4765b4f9f144aa68ef1447936c458e9
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029536B2

Reaction notes

Loading…