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

HRID 926478Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

Sodium methoxide (741 mg, 13.7 mmol) was added to a solution of 3-(4-(1H-1,2,4-triazol-1-yl)benzyl)-2,4-dichloro-6-iodoquinoline (1.1 g, 2.3 mmol, Intermediate 20: step b) in toluene (11 mL) with stirring. The mixture was heated to 105° C. After 2 hours, additional sodium methoxide (250 mg, 4.6 mmol) was added. After 3 hours, the flask was allowed to cool to 23° C. Dichloromethane (50 mL) was added and then the mixture was filtered through Celite®. The filter cake was washed with dichloromethane. The filtrate was concentrated to provide the title compound as a white solid.

Workup

waitAfter 3 hours
temperatureto cool to 23° C
filtrationthe mixture was filtered through Celite®
washThe filter cake was washed with dichloromethane
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-a15ebd374bff47b7825e77c066d3cfc3
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284308B2

Reaction notes

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