Isoprene → HCID 66587516, compound

HRID 2047700Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[F:18])[CH:5]=[N:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[N:11][CH:12]=1.[CH2:19]=[CH:20][C:21](=[CH2:23])[CH3:22]>CC#N.FC(F)(F)S([O-])(=O)=O.[Sc+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[CH2:22][C:21]([CH3:23])([CH:20]=[CH2:19])[C:12]3[N:11]=[C:10]([C:13]#[N:14])[CH:9]=[CH:8][C:7]=3[NH:6]2)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution 5-[(3-chloro-4-fluoro-benzylidene)-amino]-pyridine-2-carbonitrile (3.7 g, 14.3 mmol) in MeCN (36 mL) were added isoprene (5.8 mL, 57.1 mol) and scandium(III) trifluoromethanesulfonate (Sc(OTf)3) (1.4 g, 2.9 mmol). The resulting mixture was stirred at 80° C. for 16 hours in sealed tube. The mixture was extracted with diethyl ether (80 mL) and washed with water (100 mL) and brine (100 mL) and then dried over anhydrous Na2SO4. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 0-20% ethyl acetate in petroleum ether) to afford 6-(3-chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carbonitrile (0.25 g, 5.5%) as white powder. MS (ESI+) [(M+H)+] 328.2.

Workup

extractionThe mixture was extracted with diethyl ether (80 mL)
washwashed with water (100 mL) and brine (100 mL)
dry with materialdried over anhydrous Na2SO4
customThe solvent was removed in vacuo
customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 0-20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-415ea3e4a9ad422bb8f88c09fd1f8c61
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592594B2

Reaction notes

Loading…