Potassium Phosphate, Tribasic → 2-(Dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine

HRID 71075Notes

Reaction equation

HRID 71075 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)[N:3]=1.[CH:16]1[C:24]2[C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21][C:20]=2[C:19](B(O)O)=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>O.C(COC)OC>[CH:16]1[C:24]2[C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21][C:20]=2[C:19]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=3)[N:3]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 2734329Dibenzothiophene-4-boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 594893042-Chloro-6-(3-methoxyphenyl)pyridine

Product 1

HCID 594892612-(Dibenzo[b,d]thiophen-4-yl)-6-(3-methoxyphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-chloro-6-(3-methoxyphenyl)pyridine (3.5 g, 16 mmol), dibenzothiophene-4-boronic acid (4 g, 17.5 mmol), potassium phosphate (10.2 g, 48 mmol), dimethoxyethane 500 mL and water 50 mL was prepared. Nitrogen was bubbled directly in the mixture for 15 minutes. Next tris dibenzylideneacetone dipalladium (147 mg, 0.16 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (263 mg, 0.64 mmol) were added, and then nitrogen was bubbled in the mixture for another 15 minutes. The reaction mixture was heated to reflux overnight under nitrogen. The next day the reaction mixture was cooled to room temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and evaporated. The mixture was purified by silica column with up to 10% ethyl acetate in hexanes to gain 3.8 g yellow solid (65%).

Workup

  1. customwas prepared
  2. customNitrogen was bubbled directly in the mixture for 15 minutes
  3. customnitrogen was bubbled in the mixture for another 15 minutes
  4. temperatureThe reaction mixture was heated
  5. temperatureto reflux overnight under nitrogen
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with dichloromethane
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated
  11. customThe mixture was purified by silica column with up to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6bdbff3db27e41ebb229e24e6305aeb0
Source dataset
uspto-grants-2014_09
Patent number
US08822708B2

Reaction notes

Loading…