Sodium Carbonate → 2-Phenylpyridin-4-amine

HRID 917457Notes

Reaction equation

HRID 917457 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[C:9]1([C:2]2[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 844322-Chloropyridin-4-amine

Product 1

HCID 27628332-Phenylpyridin-4-amineYield 87.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 16.0 g (124 mmol) 2-chloro-4-aminopyridine in 200 ml toluene were added 18.2 g (149 mmol) phenylboronic acid, 7.19 g (6.22 mmol) tetrakis(triphenylphosphine)palladium(0) and 130 ml (260 mmol) 2 M aq. sodium carbonate solution. The mixture was heated at 100° C. for 16 h and then cooled to room temperature and extracted three times with ethyl acetate. The combined organic phases were extracted three times with 200 ml 1 M aq. hydrochloric acid. The combined acid extracts were then made alkaline by addition of 5 M aq. sodium hydroxide solution and extracted three times with dichloromethane. The combined organic extracts were dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (acetone) followed by trituration in hexane containing a little ether afforded 18.5 g (87%) 2-phenyl-pyridin-4-ylamine as a white solid. ES-MS m/e (%): 171 (M+H+, 100).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted three times with ethyl acetate
  3. extractionThe combined organic phases were extracted three times with 200 ml 1 M aq. hydrochloric acid
  4. additionby addition of 5 M aq. sodium hydroxide solution
  5. extractionextracted three times with dichloromethane
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f93ae24f3ed46d3b614cd18c8ec8f49
Source dataset
uspto-grants-2007_09
Patent number
US07273865B2

Reaction notes

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