Cyclohexene → 6-((4-fluorotetrahydro-2H-pyran-4-yl)methoxy)pyridine-3-sulfonamide

HRID 2168055Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:5]=[N:6][C:7]=1[O:8][CH2:9][C:10]1([F:16])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C1CCCCC=1>C(OCC)(=O)C.[Pd]>[F:16][C:10]1([CH2:9][O:8][C:7]2[N:6]=[CH:5][C:4]([S:17]([NH2:20])(=[O:18])=[O:19])=[CH:3][CH:2]=2)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of 5-bromo-6-((4-fluorotetrahydro-2H-pyran-4-yl)methoxy)pyridine-3-sulfonamide (200 mg) and cyclohexene (0.549 mL) in ethyl acetate (10 mL) was added 10% palladium on carbon (57.6 mg). The suspension was stirred for 60 minutes at 120° C. The reaction mixture was filtered and concentrated. The product was purified by reverse-phase flash chromatography (C18, 150 g, 10%-100% acetonitrile/H2O/trifluoroacetic acid 0.1%).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated
customThe product was purified by reverse-phase flash chromatography (C18, 150 g, 10%-100% acetonitrile/H2O/trifluoroacetic acid 0.1%)

Sources & evidence

ORD record: ord-0bac792615e24609b32f33a1ecc3281d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045475B2

Reaction notes

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