Iodoethane → HCID 67015651, compound

HRID 1617972Notes

Reaction equation

HRID 1617972 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[CH:4][CH:3]=1.[OH-:27].[K+].C(P([C:55]([CH3:58])(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.ICC>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([O:27][CH2:55][CH3:58])=[CH:7][CH:6]=2)[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([CH3:18])[CH:13]=2)=[O:11])=[C:20]([CH3:26])[CH:21]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 14797Potassium HydroxideHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 66667222HCID 66667222, compound

Product 1

HCID 67015651HCID 67015651, compound

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

In analogy to example 364, step 1, from (S)-3-(4-bromo-phenyl)-3-(4-chloro-2-methyl-phenyl)-1-(2-methyl-pyridin-4-yl)-propan-1-one in presence of potassium hydroxide, 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, tris(dibenzylideneacetone)dipalladium(0), cetyl trimethylammonium bromide and iodoethane was prepared the title compound as a yellow foam, MS (ESI+): m/z=394.0 ([M+H]+).

Sources & evidence

ORD record
ord-210c7167ee6444ecaeb436251271f7c2
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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