Dichloromethane → 3-(4-(1H-Imidazol-1-yl)benzyl)-4-chloro-6-iodo-2-methoxyquinoline

HRID 926474Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

A heterogeneous mixture containing 3-(4-(1H-imidazol-1-yl)benzyl)-2,4-dichloro-6-iodoquinoline (1.2 g, 2.5 mmol, Intermediate 17: step b) and sodium methoxide (1.6 g, 30 mmol) in toluene (25 mL) was heated to 110° C. After 2 hours, the flask was allowed to cool to 23° C. Dichloromethane (100 mL) was added and the mixture was filtered through Celite®, rinsing the filter cake with dichloromethane. The filtrate was concentrated to provide the title compound as an off-white solid. This material was used without further purification.

Workup

temperatureto cool to 23° C
filtrationthe mixture was filtered through Celite®
washrinsing the filter cake with dichloromethane
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-588ce605ed554b268eb616235dd3206f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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