Potassium Carbonate → HCID 90403195, compound

HRID 1049257Notes

Reaction equation

HRID 1049257 reaction equation
Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[CH3:8].[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][C:2]2[C:3]([CH3:12])=[N:4][C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=2[CH3:8])[CH:17]=[CH:16][N:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90403338HCID 90403338, compoundHCID 178516507HCID 178516507, compound

Product 1

HCID 90403195HCID 90403195, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 3-bromo-2,4-dimethyl-6-nitropyridine (1.00 g, 4.33 mmol), 2-chloropyridin-4-ol (1.12 g, 8.66 mmol) and K2CO3 (1.79 g, 12.98 mmol) in DMA (5 mL) was sparged with Ar, heated at 105° C. overnight, then cooled to RT. The mixture was diluted with EtOAc, washed successively with 10% K2CO3, 5% LiCl, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-((2-chloropyridin-4-yl)oxy)-2,4-dimethyl-6-nitropyridine (245 mg, 20%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.31 (d, J=5.2 Hz, 2H), 7.15 (d, J=2.3 Hz, 1H), 7.01 (dd, J=5.8, 2.3 Hz, 1H), 2.33 (s, 3H), 2.23 (s, 3H); MS (ESI) m/z: 280.0 (M+H+).

Workup

  1. customwas sparged with Ar
  2. temperaturecooled to RT
  3. additionThe mixture was diluted with EtOAc
  4. washwashed successively with 10% K2CO3, 5% LiCl
  5. dry with materialbrine, dried over Na2SO4
  6. concentrationconcentrated to dryness
  7. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-30c08608081846c2ad7cbedea840db9e
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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