Diethyl Ether → HCID 11241348, compound

HRID 1941504Notes

Reaction equation

HRID 1941504 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.B(O)(O)[C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[CH:16][CH:17]=1.CCOCC>C(=O)([O-])[O-].[Na+].[Na+].C(COC)OC.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>[N+:8]([C:7]1[C:2]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 796132-Chloro-3-nitropyridineHCID 79799Tolylboronic acid

Product 1

HCID 11241348HCID 11241348, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A stirred mixture of 2-chloro-3-nitropyridine (10.6 g), p-tolylboronic acid (19.69 g) and tetrakis(triphenylphosphine)palladium (O) (0.16 g) in 2N sodium carbonate solution (100 ml) and dimethoxyethane (100 ml) was heated to reflux under nitrogen. After 64 h the mixture was cooled then filtered through hyflo eluting with more dimethoxyethane. The filtrate was evaporated in vacuo to give an oil which was redissolved with ether (300 ml) and washed with 5N sodium hydroxide solution (300 ml). The aqueous portion was further extracted with ether (300 ml×2). The combined organic extracts ware washed with water (200 ml), 1N hydrochloric acid (2×100 ml) and saturated brine. were dried (MgSO4) and evaporated in vacuo. The resultant crystalline solid was triturated with hexane to give the title compound as a yellow crystalline solid (11.66 g). T.l.c.(Hexanelethylacetate (2:1)), Rf 0.52,

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen
  3. temperatureAfter 64 h the mixture was cooled
  4. filtrationthen filtered through hyflo
  5. washeluting with more dimethoxyethane
  6. customThe filtrate was evaporated in vacuo
  7. customto give an oil which
  8. washwashed with 5N sodium hydroxide solution (300 ml)
  9. extractionThe aqueous portion was further extracted with ether (300 ml×2)
  10. washThe combined organic extracts ware washed with water (200 ml), 1N hydrochloric acid (2×100 ml) and saturated brine
  11. dry with materialwere dried (MgSO4)
  12. customevaporated in vacuo
  13. customThe resultant crystalline solid was triturated with hexane

Sources & evidence

ORD record
ord-70eb2f5420bc40c08810caf57a99f5bf
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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