(4-Bromophenyl)boronic acid → 3-(4-Bromophenyl)-1-(6-methoxypyridin-3-yl)-3-(4-methylthiazol-5-yl)propan-1-one

HRID 1617901Notes

Reaction equation

HRID 1617901 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH3:17])=[CH:5][CH:4]=1.[Br:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.O.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([CH:11]([C:12]2[S:16][CH:15]=[N:14][C:13]=2[CH3:17])[CH2:10][C:9]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:18])=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 79599(4-Bromophenyl)boronic acidHCID 516892Sodium BicarbonateHCID 66667367HCID 66667367, compound

Product 1

HCID 666668163-(4-Bromophenyl)-1-(6-methoxypyridin-3-yl)-3-(4-methylthiazol-5-yl)propan-1-one

Reagents, catalysts & solvents 3

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

In analogy to example 203, step 1, (E)-1-(6-methoxypyridin-3-yl)-3-(4-methylthiazol-5-yl)prop-2-en-1-one was reacted with 4-bromophenylboronic acid in the presence of chloro(1,5-cyclooctadiene)rhodium(I) dimer and sodium hydrogencarbonate in 1,4-dioxane and water at 60° C. to give the title compound as a yellow solid, MS (ESI+): m/z=419.1 [M+H]+.

Sources & evidence

ORD record
ord-848b22e718ce44cabc902af2753febb1
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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