Sodium Carbonate → 5-(4-Fluorophenyl)-3-nitropyridin-2-amine

HRID 2246412Notes

Reaction equation

HRID 2246412 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1388782-Amino-5-bromo-3-nitropyridineHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 219560765-(4-Fluorophenyl)-3-nitropyridin-2-amineYield 76%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-amino-5-bromo-3-nitropyridine (2.2 g, 10.1 mmol) in dimethoxyethane (20 mL) were added 4-fluorophenylboronic acid (4.83 g, 13.1 mmol), tetrakis(triphenylphosphine)palladium (580 mg, 0.50 mmol) and 2N aqueous sodium carbonate solution (10 mL). The mixture was stirred at 80° C. for 9 hours under a nitrogen atmosphere. After the reaction mixture was cooled to room temperature, it was diluted with ethyl acetate to give a precipitate, which was collected by filtration, washed with ethyl acetate and then dried to give the title compound (1.76 g, 76%).

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customto give a precipitate, which
  3. filtrationwas collected by filtration
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-723084d23a104e158c2b0fc40c371a41
Source dataset
uspto-grants-2010_03
Patent number
US07687514B2

Reaction notes

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