Alpha-Methylstyrene → HCID 70497572, compound

HRID 2407975Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[F:21])[CH:16]=O.[C:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:24])=[CH2:23].F[C:32](F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:2][C:3]([C:4]1[CH:5]=[C:6]2[C:7](=[CH:8][CH:9]=1)[NH:10][CH:16]([C:15]1[CH:18]=[CH:19][C:20]([F:21])=[C:13]([Cl:12])[CH:14]=1)[CH2:23][C:22]2([CH3:24])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:11])[CH3:32]

Participants

Conditions

Temperature: 90 °C

Procedure

To a stirred solution of 4-amino-benzoic acid methyl ester (0.825 g, 5 mmol) and 3-chloro-4-fluoro-benzaldehyde (869 mg, 5.5 mmol) in acetonitrile (50 mL) were added isopropenyl-benzene (2.36 g, 20 mmol) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (465 mg, 0.75 mmol). The resulting mixture was stirred at 90° C. for 16 h in sealed tube. The mixture was diluted with ethyl acetate (50 mL) and washed with water (30 mL×2) and brine (30 mL×2) and then dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether) to afford 2-(3-chloro-4-fluoro-phenyl)-4-methyl-4-phenyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (850 mg, 40%) as a light yellow solid: MS (ESI) M+1=424.2.

Workup

washwashed with water (30 mL×2) and brine (30 mL×2)
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed in vacuo
customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 10-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-af421406559a48eeab856ef30abfaa92
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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