Lithium Chloride → Methyl 2-(2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)phenyl)propanoate

HRID 326921Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:20]([OH:23])[CH:21]=[CH2:22])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Li]OC(C)=O.O.[Li+].[Cl-].I[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41].C([O-])(O)=O.[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:23])[CH2:21][CH2:22][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[CH:39]([CH3:44])[C:40]([O:42][CH3:43])=[O:41])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A degassed suspension of the product of Step 1 (15.0 g, 46.6 mmol), n-Bu4NCl (25.9 g, 93 mmol), LiOAc.H2O (7.7 g, 115 mmol), LiCl (1.98 g, 93 mmol), Pd(OAc)2 (0.315 g, 1.4 mmol), and methyl 2-(2-iodophenyl)propanoate in DMF (90 mL) was stirred for 2 hours at 100° C. The dark red solution was then cooled to 0° C. and poured into saturated NaHCO3 solution (500 mL). The product was extracted with EtOAc and the organic layer was washed with H2O followed by brine. The solvent was removed under vacuum and the residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10) to give a pale yellow foam (18.9 g).

Workup

temperatureThe dark red solution was then cooled to 0° C.
extractionThe product was extracted with EtOAc
washthe organic layer was washed with H2O
customThe solvent was removed under vacuum
customthe residue was purified by flash chromatography (EtOAc:hexane 1:10, 1:5 and 3:10)

Sources & evidence

ORD record: ord-92b426f88db14f86b87e9bbb6c316fc3
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270324

Reaction notes

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