Isobutylene → HCID 70496195, compound

HRID 2408086Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[NH2:11].[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O.O.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.[CH2:48]=[C:49]([CH3:51])[CH3:50]>C(#N)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]2[C:5]=1[NH:11][CH:17]([C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([Br:13])[CH:15]=1)[CH2:48][C:49]2([CH3:51])[CH3:50])=[O:12]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-amino-5-fluoro-benzoic acid methyl ester (12.1 g, 71.4 mmol), 3-bromo-benzaldehyde (13.2 g, 71.4 mmol) and ytterbium(III) triflate hydrate (4.4 g, 71.4 mmol) in acetonitrile (200 mL) was cooled to 0° C. in a sealed reaction bottle. Then a cooled solution of isobutene (28 g, 500 mmol) was added into. The reaction mixture was heated to 90° C. and stirred for 12 h. The solvent was removed in vacuo and the residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (20% ethyl acetate/hexanes) to afford 2-(3-bromo-phenyl)-6-fluoro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (16 g, 57%) as a white solid: MS (ESI) M+1=392.1.

Workup

temperatureThe reaction mixture was heated to 90° C.
customThe solvent was removed in vacuo
customthe residue was purified on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-cd7866db0cae4a37b46bb5253ef9a4aa
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809369B2

Reaction notes

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