Hexane → [4-(3-Chlorophenyl)-2-methoxy-6-quinolinyl](3-iodophenyl)-methanone

HRID 346983Notes

Reaction equation

[Li]CCCC.CCCCCC.Br[C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[C:18]([O:23][CH3:24])[CH:17]=[C:16]2[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1.[I:32][C:33]1[CH:34]=[C:35]([CH:42]=[CH:43][CH:44]=1)[C:36](N(OC)C)=[O:37]>C1COCC1.CCOC(C)=O>[Cl:31][C:27]1[CH:26]=[C:25]([C:16]2[C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:36]([C:35]4[CH:42]=[CH:43][CH:44]=[C:33]([I:32])[CH:34]=4)=[O:37])[CH:14]=3)[N:19]=[C:18]([O:23][CH3:24])[CH:17]=2)[CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: -70 °C

Procedure

BuLi 1.6M in hexane (0.0334 mol) was added dropwise at −70° C. to a solution of 6-bromo-4-(3-chlorophenyl)-2-methoxy-quinoline (0.0304 mol) in THF (100 ml), under N2 flow. The mixture was stirred at −70° C. for 10 minutes. A solution of 3-iodo-N-methoxy-N-methyl-benzamide (0.0274 mol) in THF (40 ml) was added dropwise. The mixture was stirred at −70° C. for 1 hour and poured out into ice water. EtOAc was added. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated, yielding 16.5 g (100%) of [4-(3-chlorophenyl)-2-methoxy-6-quinolinyl](3-iodophenyl)-methanone (intermediate 73). This product was used without further purification in the next reaction step.

Workup

stirringThe mixture was stirred at −70° C. for 1 hour
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated

Sources & evidence

ORD record: ord-919fb3fc0bfc41c4b991cbcbf9f31777
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173040B2

Reaction notes

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