Sodium Carbonate → N-(3-(4-Cyanophenyl)phenyl)pyrid-3-ylmethylamine

HRID 392453Notes

Reaction equation

HRID 392453 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][CH2:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)#[N:17].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.ClCCl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[C:4]([NH:8][CH2:9][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=2)=[CH:20][CH:19]=1)#[N:17]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 226638983-Bromo-N-(pyridin-3-ylmethyl)aniline

Product 1

HCID 69880749N-(3-(4-Cyanophenyl)phenyl)pyrid-3-ylmethylamine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(3-bromophenyl)pyridin-3-ylmethylamine (364 mg, 1.38 mmol), 4-cyanophenylboronic acid (305 mg, 2.08 mmol), sodium carbonate (2.15 ml of a 2M aqueous solution, 4.3 mmol), and tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.061 mmol), under a nitrogen atmosphere was refluxed in dioxane (15 ml) for 6 h, then cooled to room temperature. The mixture was diluted with dichloromethane (70 ml) and water (15 ml). The organics were separated, dried over sodium sulfate, filtered, and concentrated to a brown solid. The solid was purified by radial chromatography eluting with 2 to 4% methanol/dichloromethane to afforded the title compound. MS calcd. 285.3; MS (M+1) 286.3.

Workup

  1. customThe organics were separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a brown solid
  5. customThe solid was purified by radial chromatography
  6. washeluting with 2 to 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-729aa765c3924c68a48fac9752a46f13
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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