Isobutylene → HCID 70496137, compound

HRID 2407985Notes

Reaction equation

[N:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O.[CH2:26]=[C:27]([CH3:29])[CH3:28].FC(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>[Br:17][C:18]1[CH:19]=[C:20]([CH:21]2[CH2:26][C:27]([CH3:29])([CH3:28])[C:12]3[C:13](=[CH:14][CH:15]=[C:10]([S:7]([N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)(=[O:9])=[O:8])[CH:11]=3)[NH:16]2)[CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 4-(morpholine-4-sulfonyl)-phenylamine (3 g, 12.4 mmol) and 3-bromo-benzaldehyde (2.52 g, 13.6 mmol) in acetonitrile (150 mL) were added isobutene (2.7 mL, 37.2 mmoll) and ytterbium(III) trifluoromethanesulfonate (Yb(OTf)3) (1.54 g, 2.5 mmol). The resulting mixture was stirred at 80° C. for 18 h in sealed tube. The mixture solution was diluted with ethyl acetate (300 mL) and washed with water (100 mL×2) and brine (100 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, 10-40% ethyl acetate in petroleum ether) to afford 2-(3-bromo-phenyl)-4,4-dimethyl-6-(morpholine-4-sulfonyl)-1,2,3,4-tetrahydro-quinoline (2.7 g, 47.4%) as a light yellow solid: MS (ESI) M+1=465.0 & 467.0.

Workup

washwashed with water (100 mL×2) and brine (100 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, 10-40% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-db0de250769e4e7f9cc7489a59338511
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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