Sodium Carbonate → HCID 61029678, compound

HRID 1454809Notes

Reaction equation

HRID 1454809 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.[Pd].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>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3008092-Amino-6-bromopyridineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 61029678HCID 61029678, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 21863594Toluene ethanolSolvent

Procedure

2-Amino-6-bromopyridine (1 g) and 2-chlorophenylboronic acid (1.039 g) were dissolved in toluene/ethanol (30 mL/3 mL) and at RT under an argon atmosphere treated with 2N aqueous sodium carbonate solution (6.13 mL). The mixture was stirred for 30 minutes at RT then treated with tetrakis(triphenylphosphine) palladium(0), 0.267 g, and heated to reflux for 24 h. The mixture was then cooled to RT and partitioned between AcOEt and water, the layers were separated and the organic layer dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 4:1) to give 6-(2-chloro-phenyl)-pyridin-2-ylamine as white solid (0.632 g). MS (EI): 204 (M+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. temperatureThe mixture was then cooled to RT
  4. custompartitioned between AcOEt and water
  5. customthe layers were separated
  6. dry with materialthe organic layer dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (heptane/AcOEt 4:1)

Sources & evidence

ORD record
ord-23049043f4c74b4f9635a2c8f816f6ae
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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