Sodium Carbonate → 3-Bromo-5-(3,4-dichlorophenyl)-4-amino-pyridine

HRID 488721Notes

Reaction equation

HRID 488721 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:9])[C:7]=1[NH2:8].C([O-])([O-])=O.[Na+].[Na+].[Cl:16][C:17]1[C:18]([Cl:26])=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1.C(O)C.C(OCC)(=O)C.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>[Br:9][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[C:18]([Cl:26])[CH:19]=2)[C:7]=1[NH2:8]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 6197924-Amino-3,5-dibromopyridineHCID 27346612,3-Dichlorobenzeneboronic acid

Product 1

HCID 222673173-Bromo-5-(3,4-dichlorophenyl)-4-amino-pyridine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3,5-dibromo-4-amino-pyridine 1 (4.0 g, 15.87 mmol), Pd(PPh3)4 (0.91 g, 0.78 mmol) and aqueous solution of Na2CO3 (23.8 ml, 2M) in toluene (80 ml) is added to a solution of dichlorobenzene boronic acid (6.23 g, 46.4 mmole) in ethanol (24 ml). The mixture is refluxed for 14 h., diluted with ethyl acetate and washed with saturated NH4Cl solution. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel to give 2.

Workup

  1. temperatureThe mixture is refluxed for 14 h.
  2. washwashed with saturated NH4Cl solution
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel
  6. customto give 2

Sources & evidence

ORD record
ord-0b5ac5e1d3264deeb2e49a2f83b3b173
Source dataset
uspto-grants-2005_12
Patent number
US06974808B2

Reaction notes

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