Methyl iodide → HCID 67291515, compound

HRID 1036875Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].I[CH3:27]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16]([CH3:19])([CH3:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([F:23])([F:21])[F:22])[CH:14]=3)[N:9]2[CH3:27])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 2-(3-bromo-phenyl)-4,4-dimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (5.0 g, 13.06 mmol) in N,N-dimethylformamide (15 mL) was added a 60% dispersion of sodium hydride in mineral oil (1.1 g, 26.1 mmol) portionwise at 0° C. The mixture was stirred at 0° C. for 30 min and then iodomethane (2.5 mL, 39.2 mmol) was added to the above mixture dropwise at 0° C. The solution was stirred at 0° C. for 2 h and then extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The yellowish residue was purified by ISCO combi-flash chromatography (gradient elution, 10% ethyl acetate/hexane) to afford 2-(3-bromo-phenyl)-1,4,4-trimethyl-6-trifluoromethyl-1,2,3,4-tetrahydro-quinoline (3.6 g, 70%) as a yellow oil: MS obsd. (ESI+) [(M+H)+] 397.9 & 399.9.

Workup

stirringThe solution was stirred at 0° C. for 2 h
extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe yellowish residue was purified by ISCO combi-flash chromatography (gradient elution, 10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-14122eb571954f999332ee4f53292418
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546427B2

Reaction notes

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