Potassium Phosphate, Tribasic → HCID 90402879, compound

HRID 1049260Notes

Reaction equation

HRID 1049260 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O1CCOCC1.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]>[CH3:18][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:23]3[CH:24]=[C:20]([CH3:19])[N:21]=[CH:22]3)[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridineHCID 178418800HCID 178418800, compound

Product 1

HCID 90402879HCID 90402879, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of Pd2(dba)3 (0.172 g, 0.188 mmol) and Me4t-BuXPhos (0.181 g, 0.376 mmol) in toluene (2 mL) and dioxane (4 mL) was heated at 120° C. for 3 min, cooled to RT, added to a degassed suspension of Example A4 (2.500 g, 9.41 mmol), 4-methyl imidazole (1.00 g, 12.18 mmol) and K3PO4 (4.00 g, 18.82 mmol) in toluene (4 mL) and dioxane (8 mL) and heated at 110° C. overnight. The mixture was cooled to RT, the solids were removed via filtration and washed with THF, and the filtrate was concentrated to dryness and purified via silica gel chromatography (EtOAc/DCM) to afford 2-methyl-3-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.52 g, 52%). 1H NMR (400 MHz, DMSO-d6): δ 8.41 (m, 2H), 8.25 (d, J=8.7 Hz, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.64 (t, J=1.3 Hz, 1H), 7.47 (d, J=2.2 Hz, 1H), 7.04 (dd, J=5.7, 2.2 Hz, 1H), 2.49 (s, 3H), 2.13 (s, 3H); MS (ESI) m/z: 312.1 (M+H+).

Workup

  1. temperatureheated at 110° C. overnight
  2. temperatureThe mixture was cooled to RT
  3. customthe solids were removed via filtration
  4. washwashed with THF
  5. concentrationthe filtrate was concentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/DCM)

Sources & evidence

ORD record
ord-09735b078ae34165a56f928cb9c57fb6
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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