Methyl iodide → HCID 23004035, compound

HRID 396354Notes

Reaction equation

[N:1]1([CH2:7][CH:8]([C:10]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([C:24]([F:27])([F:26])[F:25])[CH:11]=2)[OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CI.[C:32]([O-])(O)=O.[Na+]>C1COCC1>[CH3:32][O:9][CH:8]([C:10]1[C:19]2[C:14](=[C:15]([C:20]([F:21])([F:22])[F:23])[CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([C:24]([F:27])([F:25])[F:26])[CH:11]=1)[CH2:7][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cold solution of α-piperidinomethyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol (60 mg, 0.15 mmol) in THF (1.5 mL) was added NaH (6 mg, 60% dispersion in oil, 0.15 mmol), the mixture stirred at 0° C. for 30 min, treated with methyl iodide (10 μL, 0.16 mmol), allowed to warm to room temperature and stirred for 1 h. The reaction mixture was poured into saturated NaHCO3, extracted with EtOAc (2×20 mL), the combined extracts dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2, EtOAc] to give the title compound (62 mg, 100%) as a pale yellow oil: IR νmax (Nujol)/cm−1 2937, 2855, 2824, 1603, 1585, 1309, 1188, 1147, 1108 and 769; NMR δH (400 MHz, CDCl3) 1.40-1.45 (2H, m), 1.52-1.66 (4H, m), 2.44-2.61 (5H, m), 2.84 (1H, dd, J 13.9, 7.8 Hz), 5.14 (1H, dd, J 7.8, 3.3), 7.74 (1H, t, J 7.7 Hz), 7.92 (1H, s), 8.17 (1H, d, J 6.9 Hz) and 8.45 (1H, d, J 8.5 Hz).

Workup

temperatureto warm to room temperature
stirringstirred for 1 h
extractionextracted with EtOAc (2×20 mL)
dry with materialthe combined extracts dried (MgSO4)
concentrationconcentrated in vacuo
custompurified by chromatography [SiO2, EtOAc]

Sources & evidence

ORD record: ord-19fe4cc03dc74aecb30ea3a22bdb2479
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06608085B1

Reaction notes

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