Potassium Phosphate, Tribasic → 8-(4-(3,4-Difluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine

HRID 1844931Notes

Reaction equation

HRID 1844931 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][C:34]([F:37])=[C:33]([F:38])[CH:32]=2)[CH:28]=[CH:27][N:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[F:38][C:33]1[CH:32]=[C:31]([C:29]2[CH:28]=[CH:27][N:26]=[C:25]([C:14]3[C:9]4[O:8][C:6]5[C:5]([C:10]=4[CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=5)[CH:30]=2)[CH:36]=[CH:35][C:34]=1[F:37]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 115503572-Chloro-4-(3,4-difluorophenyl)pyridineHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine

Product 1

HCID 901216158-(4-(3,4-Difluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridineYield 65.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (3.0 g, 9.70 mmol), 2-chloro-4-(3,4-difluorophenyl)pyridine (2.41 g, 10.67 mmol), Pd2(dba)3 (0.178 g 0.194 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.319 g, 0.776 mmol), potassium phosphate (7.21 g, 34.0 mmol), toluene (70 mL) and water (7 mL) was degassed with nitrogen and then refluxed overnight. The mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then further purified by column chromatography using ethyl acetate in dichloromethane to give 8-(4-(3,4-difluorophenyl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.36 g, 6.34 mmol, 65.3% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried on Na2SO4
  6. customfurther purified by column chromatography

Sources & evidence

ORD record
ord-4e0ecaaa8aaf4257b8b052e56ecc9a29
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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