4-Chloro-6,7-dimethoxyquinoline → 4-[2-Fluoro-4-(6-phenoxy-pyridazin-3-yl)-phenoxy]-6,7-dimethoxy-quinoline

HRID 1993369Notes

Reaction equation

HRID 1993369 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[C:21]([C:23]2[N:24]=[N:25][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][CH:28]=2)[CH:20]=[CH:19][C:18]=1[OH:36]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1>[F:16][C:17]1[CH:22]=[C:21]([C:23]2[N:24]=[N:25][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][CH:28]=2)[CH:20]=[CH:19][C:18]=1[O:36][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 1360707052-Fluoro-4-(6-phenoxy-pyridazin-3-yl)-phenol

Product 1

HCID 118575084-[2-Fluoro-4-(6-phenoxy-pyridazin-3-yl)-phenoxy]-6,7-dimethoxy-quinoline

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chloro-6,7-dimethoxy-quinoline (0.4 g, 1.79 mmol), 2-fluoro-4-(6-phenoxy-pyridazin-3-yl)-phenol (Step 2, 0.50 g, 1.79 mmol) and DMAP (0.22 g, 1.79 mmol) in 6 mL of toluene (in microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 180° C. for 1 h.

Sources & evidence

ORD record
ord-9f9b7c037ca44077b586972fead6cf5d
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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