Cesium carbonate → HCID 66915386, compound

HRID 1850033Notes

Reaction equation

HRID 1850033 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH2:9]([N:16]1[CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])(=O)C.[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:9]([N:16]1[CH:20]=[C:19]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)[CH:18]=[N:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 115221-Bromo-4-iodobenzeneHCID 517044Potassium AcetateHCID 27347711-Benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Product 1

HCID 66915386HCID 66915386, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

4-Bromo-iodobenzene (240 mg, 0.8 mmol, 1.2 eq.), 1-benzylpyrazole-4-boronic acid pinacol ester (200 mg, 0.7 mmol), potassium acetate (70 mg, 1 eq.), Pd(dppf)Cl2 (70 mg, 0.1 eq.), and Cs2CO3 (700 mg, 3.0 eq.) in DMSO (5 mL) were heated under argon at 80° C. during 1 h. The reaction mixture was extracted from water into diethyl ether, dried over Na2SO4, concentrated, and chromatographed on silica gel (5→10% EtOAc/hexanes) to give 1-benzyl-4-(4-bromophenyl)pyrazole (218 mg, 99%).

Workup

  1. extractionThe reaction mixture was extracted from water into diethyl ether
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customchromatographed on silica gel (5→10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dce7fce5291740b0ac3004ae54fae9da
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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