Potassium Carbonate → HCID 86658616, compound

HRID 1517000Notes

Reaction equation

HRID 1517000 reaction equation
[Cl:1][C:2]1[C:7]([N:8]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:6](I)[CH:5]=[CH:4][N:3]=1.[CH3:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.[Pd].P.P.P.P>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[O:30][CH3:29])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 58479601HCID 58479601, compound

Product 1

HCID 86658616HCID 86658616, compoundYield 78.3%

Reagents, catalysts & solvents 2

HCID 86658617HCID 86658617, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-chloro-4-iodo-N-(triphenylphosphoranylidene) pyridin-3-amine (12 g, 23 mmol), (2-methoxyphenyl) boronic acid (4.25 g, 28 mmol), 2M potassium carbonate solution (46.6 ml, 93 mmol) were poured in 120 mL DME and degassed with bubbling nitrogen for 15 min. To the stirred solution was added tetrakisphosphine palladium(0) (1.35 g, 1.12 mmol) and reaction mixture was degassed for another 10 min. Reaction mixture was then refluxed for 48 h. Cooled reaction mixture was partitioned between ethyl acetate and brine. Organic layer was isolated, dried over anhd. Na2SO4 and purified by silica gel column chromatography using 5-30% ethyl acetate/hexanes as eluent. 2-chloro-4-(2-methoxyphenyl)pyridin-3-amine (4.3 g, 18 mmol, 78% yield) was isolated as liquid oil which turns into white crystals upon standing at room temperature.

Workup

  1. customdegassed with bubbling nitrogen for 15 min
  2. additionTo the stirred solution was added
  3. customwas degassed for another 10 min
  4. customReaction mixture
  5. temperaturewas then refluxed for 48 h
  6. temperatureCooled
  7. customreaction mixture
  8. customwas partitioned between ethyl acetate and brine
  9. customOrganic layer was isolated
  10. customdried over anhd
  11. customNa2SO4 and purified by silica gel column chromatography

Sources & evidence

ORD record
ord-40bbc5aaf6b64f6aad46ddabc68ad8f9
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

Loading…