1-Chloro-2-iodobenzene → 3-(2-Chlorophenyl)-1-(3-(2-(6,7-difluoro-2-quinolinyl)ethenyl)phenyl)-1-propanone

HRID 1755776Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:21]([OH:24])[CH:22]=[CH2:23])[CH:18]=[CH:19][CH:20]=1)[CH:6]=[CH:5]2.[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1I.[Li+].[Cl-].[Li]OC(C)=O.O.O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:23][CH2:22][C:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH:14]=[CH:13][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][C:11]([F:12])=[C:2]([F:1])[CH:3]=3)[N:8]=2)[CH:16]=1)=[O:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of the allylic alcohol of Step 3 (1.214 g, 3.75 mmol), 1-chloro-2-iodobenzene (480 FtL), Pd(OAc)2 (30 mg), LiCl (194 mg), LiOAc.2H2O (995 rag) and Bu4NCI (2.13 g) in 7.5 mL of DMF was degassed under vacuum and heated to 100° C. under N2 for 3 hr. 25% Aq. NH4OAc was then added and the product was extracted in EtOAc, dried over Na2SO4, and purified by flash chromatography with EtOAc: toluene 2.5:97.5. Yield 1.53 g, 94%.

Workup

customwas degassed under vacuum
addition25% Aq. NH4OAc was then added
extractionthe product was extracted in EtOAc
dry with materialdried over Na2SO4
custompurified by flash chromatography with EtOAc: toluene 2.5:97.5

Sources & evidence

ORD record: ord-930cef5125954df69172621cf29c67a1
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438141

Reaction notes

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