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

HRID 346972Notes

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:44]=[CH:43][C:36]([C:37](N(OC)C)=[O:38])=[CH:35][CH:34]=1>C1COCC1>[Cl:31][C:27]1[CH:26]=[C:25]([C:16]2[C:15]3[C:20](=[CH:21][CH:22]=[C:13]([C:37]([C:36]4[CH:43]=[CH:44][C:33]([I:32])=[CH:34][CH:35]=4)=[O:38])[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 (0.0316 mol) was added dropwise at −70° C. to a mixture of 6-bromo-4-(3-chlorophenyl)-2-methoxyquinoline (0.0287 mol) in TBIF (100 ml). The mixture was stirred at −70° C. for 30 minutes and a solution of 4-iodo-N-methoxy-N-methyl-benzamide (0.0244 mol) in THF (30 ml) was added. The mixture was stirred at −70° C. for 30 minutes, poured out into ice water and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 15.6 g (>100%) of [4-(3-chlorophenyl)-2-methoxy-6-quinolinyl](4-iodophenyl)methanone, (intermediate 18).This product was used without further purification.

Workup

stirringThe mixture was stirred at −70° C. for 30 minutes
extractionextracted with CH2Cl2
customThe organic layer was separated
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was evaporated till dryness

Sources & evidence

ORD record: ord-c576a0d27cf24edf9fbd454d2e2c00cb
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07173040B2

Reaction notes

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