1,2-Dimethoxyethane → HCID 59359504, compound

HRID 1910360Notes

Reaction equation

HRID 1910360 reaction equation
Br[C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>O>[C:11]1([C:2]2[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 86093998HCID 86093998, compound

Product 1

HCID 59359504HCID 59359504, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10.2 g (0.051 mol) of 2-bromo-3,4,5-trimethylpyridine was mixed with 7.86 g (0.061 mol) of phenylboronic acid, 1.8 g (0.0016 mol) of Pd(Ph3)4, 19.1 g (0.13 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-f7fc82e5b5484a158ca3180e2063cce3
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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