2-Amino-6-methylpyridine → HCID 86643866, compound

HRID 240366Notes

Reaction equation

HRID 240366 reaction equation
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[N:4]=[C:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[C:6]1([C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][C:3]2[C:2]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=3)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 4

HCID 157652-Amino-6-methylpyridineHCID 634876Binap, (A+-)-HCID 17861074HCID 17861074, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 86643866HCID 86643866, compoundYield 105.3%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

37.8 g (0.11 mol) of 2-bromo-N-(diphenylmethylene)aniline was dissolved in toluene (100 ml), and 14.6 g (0.13 mol) of 2-amino-6-picoline, 5.2 g (5.5 mmol) of tris(dibenzylideneacetone)dipalladium(0), 11.2 g (17.6 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 15.2 g (0.15 mol) of sodium-t-butoxide were added thereto. The mixture was stirred for 2 hours at 100° C. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was washed with methanol to obtain 42.1 g (yield:>99%) of N1-(diphenylmethylene)-N2-(6-methylpyridine-2-yl)benzene-1,2-diamine.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe residue was washed with methanol

Sources & evidence

ORD record
ord-d6db223438174159aca2e4548efc383a
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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