Cesium carbonate → 2'-(2,2-Dipyridin-3-ylethyl)biphenyl-3-carboxylic acid

HRID 1686084Notes

Reaction equation

HRID 1686084 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.OB(O)[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([OH:29])=[O:28].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[C:24]2[CH:32]=[CH:31][CH:30]=[C:26]([C:27]([OH:29])=[O:28])[CH:25]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27339573-Carboxyphenylboronic acidHCID 672646383,3'-[2-(2-Bromophenyl)ethane-1,1-diyl]dipyridine

Product 1

HCID 578675722'-(2,2-Dipyridin-3-ylethyl)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,3′-[2-(2-bromophenyl)ethane-1,1-diyl]dipyridine (30 mg, 0.05 mmol), 3-(dihydroxyboryl)benzoic acid (14 mg, 0.08 mmol), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (5 mg, 0.006 mmol) in THF (2.0 mL) was treated aqueous Cs2CO3 (1.0 mL of a 1 M solution, 1.0 mmol) and sealed in a 5 mL microwave reaction tube. The mixture was irradiated at 160° C. for 10 min, cooled, and the phases separated. The organic phase was blown down under a stream of N2 and purified by reverse phase chromatography to provide the title compound. ESI+MS: 381.1 [M+H]+.

Workup

  1. customsealed in a 5 mL microwave reaction tube
  2. customThe mixture was irradiated at 160° C. for 10 min
  3. temperaturecooled
  4. customthe phases separated
  5. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-11a1ac4ee1a94da78cc9c94281afd508
Source dataset
uspto-grants-2012_04
Patent number
US08148535B2

Reaction notes

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