1,2-Dimethoxyethane → 2-(4'-tert-Butyl[1,1'-biphenyl]-3-yl)pyridine

HRID 1910350Notes

Reaction equation

HRID 1910350 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:14]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].COCCOC>O>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[CH:3]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 111155062-(3-Bromophenyl)pyridine

Product 1

HCID 595940382-(4'-tert-Butyl[1,1'-biphenyl]-3-yl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

13.7 g (0.058 mol) of 2-(3-bromophenyl)pyridine was added to 12.5 g (0.070 mol) of 4-tert-butylphenylboronic acid, 3.4 g (0.003 mol) of Pd(Ph3)4, 22.0 g (0.16 mol) of K2CO3, 50 mL of DME and 50 mL of water. The reaction mixture was refluxed for 20 hours and separated on silica gel column. MS confirmed the desired product.

Workup

  1. temperatureThe reaction mixture was refluxed for 20 hours
  2. customseparated on silica gel column

Sources & evidence

ORD record
ord-771ad6cede1c489f9fb6b87c4b81cfb9
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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