Cesium carbonate → HCID 66915495, compound

HRID 1850035Notes

Reaction equation

HRID 1850035 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].[NH:10]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[C:13]=2[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]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:13]=2[CH:12]=[CH:11][NH:10]3)=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 517044Potassium AcetateHCID 27250061-Bromo-2-fluoro-4-iodobenzeneHCID 27631731H-Indole-4-boronic acid

Product 1

HCID 66915495HCID 66915495, compoundYield 83%

Reagents, catalysts & solvents 2

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

Procedure

4-Bromo-3-fluoroiodobenzene (250 mg, 0.8 mmol, 1.2 eq.), indole-4-boronic acid (110 mg, 0.7 mmol), potassium acetate (70 mg, 1 eq.), Pd(dppf)Cl2 (70 mg, 0.1 eq.), and Cs2CO3 (700 mg, 3 eq.) in DMSO (5 mL) were heated under argon at 80° C. during 1 h. The reaction mixture was extracted from water into ether, dried Na2SO4, concentrated, and chromatographed on silica gel (5→15% EtOAc/hexanes) to give 4-(4-bromo-3-fluorophenyl)indole (164 mg, 83%).

Workup

  1. extractionThe reaction mixture was extracted from water into ether, dried Na2SO4
  2. concentrationconcentrated
  3. customchromatographed on silica gel (5→15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cbafd307131b49479952e50072a60bd7
Source dataset
uspto-grants-2015_02
Patent number
US08957049B2

Reaction notes

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