Dimethyl Sulfoxide → HCID 68004132, compound

HRID 1408876Notes

Reaction equation

Cl[C:2]1[C:7]([F:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C([O-])([O-])=O.[K+].[K+].CS(C)=O>C(OCC)C>[Br:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:22][CH2:21]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a sealed vessel were added 2-chloro-3-fluoro-5-bromopyridine (1) (10.50 g, 50 mmol), N-Boc-piperazine (9.30 g, 50 mmol), K2CO3 (8.28 g, 60 mmol), and DMSO (40 mL). The resulting mixture was heated at 120° C. for 12 hrs, then cooled down and diluted with ethyl ether (200 mL). The solution was washed with water (80 mL×2), brine (100 mL), dried, and concentrated. The residue was suspended in hexanes (150 mL) and the precipitation was formed. After removed the solid, the remaining solvents which contained the desired product were evaporated and subjected to chromatography column eluted with ethyl acetate/hexanes (0-10%) to afford 4.60 g (26%) of 11 as a colorless oil which was slowly solidified to be white solid. 1H NMR (CDCl3) δ 1.48 (9 H, s), 3.43 (4 H, m), 3.54 (4 H, m), 7.39 (4 H, dd, J=1.96, 12.04 Hz), 8.05 (1 H, m). LC/MS (M+1) 361.

Workup

temperaturecooled down
washThe solution was washed with water (80 mL×2), brine (100 mL)
customdried
concentrationconcentrated
customthe precipitation
customwas formed
customAfter removed the solid
customwere evaporated
washeluted with ethyl acetate/hexanes (0-10%)

Sources & evidence

ORD record: ord-8715d2f8959e42a5b32bb5e9bf371078
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921373B2

Reaction notes

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