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

HRID 1844920Notes

Reaction equation

HRID 1844920 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]=[C:33]([CH:37]([CH3:39])[CH3:38])[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>[CH:37]([C:33]1[CH:32]=[C:31]([C:29]2[CH:30]=[CH:25][N:26]=[C:27]([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:28]=2)[CH:36]=[CH:35][CH:34]=1)([CH3:39])[CH3:38]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 901214882-Methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridineHCID 901215252-Chloro-4-(3-isopropylphenyl)pyridine

Product 1

HCID 901214988-(4-(3-Isopropylphenyl)pyridine-2-yl)-2-methylbenzofuro[2,3-b]pyridineYield 57%

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 (3.15 g, 10.2 mmol), 2-chloro-4-(3-isopropylphenyl)pyridine (2.60 g, 11.2 mmol), Pd2(dba)3 (0.187 g 0.204 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (0.335 g, 0.815 mmol), potassium phosphate (7.57 g, 35.7 mmol), toluene (90 mL) and water (9 mL) was degassed with nitrogen and then refluxed overnight. The toluene layer was dried on Na2SO4 and then further purified by column chromatography using dichloromethane in hexanes and then vacuum distilled to give 8-(4-(3-Isopropylphenyl)pyridine-2-yl)-2-methylbenzofuro[2,3-b]pyridine (2.2 g, 57% yield).

Workup

  1. customwas degassed with nitrogen
  2. temperaturerefluxed overnight
  3. dry with materialThe toluene layer was dried on Na2SO4
  4. customfurther purified by column chromatography
  5. distillationvacuum distilled

Sources & evidence

ORD record
ord-60120eac046a40a3859a9708eca3fbe1
Source dataset
uspto-grants-2015_02
Patent number
US08946697B1

Reaction notes

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