Potassium Phosphate, Tribasic → 2-Methyl-8-(4-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridine

HRID 1844921Notes

Reaction equation

HRID 1844921 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14](B4OC(C)(C)C(C)(C)O4)=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.Cl[C:25]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=[CH:27][N:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O>[CH3:1][C:2]1[N:7]=[C:6]2[O:8][C:9]3[C:14]([C:25]4[CH:30]=[C:29]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[CH:28]=[CH:27][N:26]=4)=[CH:13][CH:12]=[CH:11][C:10]=3[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27628422-Chloro-4-phenylpyridineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine

Product 1

HCID 901214912-Methyl-8-(4-phenyl-2-pyridinyl)benzofuro[2,3-b]pyridineYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (5.96 g, 19.28 mmol), 2-chloro-4-phenylpyridine (4.39 g, 23.13 mmol), tris(dibenzylideneacetone)palladium(0) (0.353 g, 0.386 mmol) and 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.8 g, 1.951 mmol) were charged into a 500 mL 2-neck flask. Potassium phosphate tribasic (12.26 g, 57.8 mmol) was then dissolved in 45 mL of water. This solution was charged into the reaction mixture. The reaction mixture was degassed with nitrogen then was heated to reflux overnight. The reaction mixture was cooled to room temperature. The toluene layer was separated and was dried over magnesium sulfate. These organics were filtered and concentrated under vacuum. The crude product was passed through a silica gel column using 70-99% toluene/heptanes followed by 5-15% ethyl acetate/toluene. Some of the impure product fractions were columned on silica gel using 5-15% ethyl acetate/DCM. All the clean product fractions were combined yielding 2-methyl-8-(4-phenylpyridin-2-yl)benzofuro[2,3-b]pyridine (5.3 g, 15.76 mmol, 82% yield).

Workup

  1. additionThis solution was charged into the reaction mixture
  2. customThe reaction mixture was degassed with nitrogen
  3. temperaturethen was heated
  4. temperatureto reflux overnight
  5. customThe toluene layer was separated
  6. dry with materialwas dried over magnesium sulfate
  7. filtrationThese organics were filtered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a825d3fbe1f84a88b22200e166c01527
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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