Sodium Carbonate → HCID 11508310, compound

HRID 1437751Notes

Reaction equation

HRID 1437751 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C.ClCCl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:23]1([C:2]2[CH:7]=[C:6]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=3)[CH:5]=[C:4]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11673270HCID 11673270, compound

Product 1

HCID 11508310HCID 11508310, compoundYield 172.4%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2,6-dichloro-pyridin-4-yl)-p-tolyl-amine (100.4 mg, 0.4 mmol) dissolved in acetonitrile (6 mL) and 2 M Na2CO3 (6 mL) was added phenylboronic acid (122.5 mg, 1 mmol) and palladium tetrakis(triphenylphosphine) (46.3 mg, 0.04 mmol). The resulting mixture was allowed to stir at reflux for 12 hours. The sample was diluted in dichloromethane and filtered through Celite™. The Celite™ was washed with dichloromethane, and the filtrate was washed two times with water and one time with brine. The organic phase was dried over potassium carbonate and concentrated by rotary evaporation. The resulting sample was dried for 12-18 hours under vacuum. Purification (Biotage Horizon HPFC chromatography system, SiO2, 70:30 hexanes:ethyl acetate) gave a brown solid (2,6-diphenyl-pyridin-4-yl)-p-tolyl-amine (116 mg, 86%).

Workup

  1. temperatureat reflux for 12 hours
  2. filtrationfiltered through Celite™
  3. washThe Celite™ was washed with dichloromethane
  4. washthe filtrate was washed two times with water and one time with brine
  5. dry with materialThe organic phase was dried over potassium carbonate
  6. concentrationconcentrated by rotary evaporation
  7. customThe resulting sample was dried for 12-18 hours under vacuum
  8. customPurification (Biotage Horizon HPFC chromatography system, SiO2, 70:30 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-d6be7cd4a35b4d41837e052123ccc7d0
Source dataset
uspto-grants-2009_11
Patent number
US07622486B2

Reaction notes

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