Sodium Carbonate → HCID 20099815, compound

HRID 1510109Notes

Reaction equation

HRID 1510109 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B(O)O>C1C=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:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 706222-Amino-5-bromopyridineHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 20099815HCID 20099815, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

A suspension of 70 mg (0.06 mmol) of tetrakis(triphenylphosphine) palladium(0) in benzene (4 ml) was treated at RT under an argon atmosphere successively with 0.35 g (2 mmol) of 2-amino-5-bromo-pyridine, 2.2 ml (4.4 mmol) of 2 M aqueous Na2CO3 solution, 0.34 g (2.2 mmol) of 2-chlorophenylboronic acid in ethanol (1 ml) and heated to reflux for 24 h. The reaction mixture was cooled and partitioned between EtOAc and water. The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc as eluent. Combination of the purified fractions and concentration in vacuo gave 0.4 g (98%) of the desired 5-(2-chloro-phenyl)-pyridin-2-ylamine as white crystalline solid. ISP mass spectrum, m/e: 205.1 (M+1 calculated for C11H9ClN2: 205).

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 h
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between EtOAc and water
  5. customThe layers were separated
  6. dry with materialthe organic layer dried over sodium sulphate
  7. concentrationconcentrated in vacuo
  8. concentrationCombination of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-68551a7fa8584d18b278bc82ab17156a
Source dataset
uspto-grants-2012_07
Patent number
US08211913B2

Reaction notes

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