Sodium Methoxide → (4-Chloro-2-methoxy-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 526839Notes

Reaction equation

Cl[C:2]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[C:10]([Cl:23])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:24]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)=[O:25])[CH:8]=2)[N:3]=1.[CH3:32][O-:33].[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:23][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:24]([C:26]3[N:30]([CH3:31])[CH:29]=[N:28][CH:27]=3)=[O:25])[CH:8]=2)[N:3]=[C:2]([O:33][CH3:32])[C:11]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 105 °C

Procedure

A mixture of (2,4-dichloro-3-(4-(methylsulfonyl)benzyl)quinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanone (0.2 g, 0.42 mmol, Intermediate 7: step d) and dry sodium methoxide (0.11 g, 2.11 mmol) in toluene (10 mL) was heated in a sealed tube at 105° C. for 6 hours. The mixture was then cooled to room temperature, diluted with DCM and stirred for 30 minutes at room temperature. The resulting suspension was filtered through Celite®, rinsing several times with DCM. The solvents were removed under reduced pressure and the residue chromatographed (heptane/DCM gradient) to provide the title compound as a white solid.

Workup

temperatureThe mixture was then cooled to room temperature
filtrationThe resulting suspension was filtered through Celite®
washrinsing several times with DCM
customThe solvents were removed under reduced pressure
customthe residue chromatographed (heptane/DCM gradient)

Sources & evidence

ORD record: ord-7b1c41a323c64284b796fa7e54041bf0
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346782B2

Reaction notes

Loading…