Sodium Carbonate → 2-Bromo-5-phenylpyridine

HRID 1960117Notes

Reaction equation

HRID 1960117 reaction equation
C([O-])([O-])=O.[Na+].[Na+].I[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][N:16]=1>CN(C=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:14][C:15]1[CH:20]=[CH:19][C:18]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:17][N:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 27627062-Bromopyridine-5-boronic acid

Product 1

HCID 27628752-Bromo-5-phenylpyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Na2CO3 (1.117 mL, 2.234 mmol) followed by Pd(PPh3)4 (51.6 mg, 0.045 mmol) were added to a solution of iodobenzene (0.1 mL, 0.894 mmol) and 2-bromopyridine-5-boronic acid (271 mg, 1.340 mmol) in DMF (4 mL). The reaction was heated at 60° C. for 4 h, cooled and concentrated. The residue was partitioned between EtOAc and water. The organic phase was washed with brine, dried (MgSO4), and concentrated. Chromatography over silica eluting with 4:1 hexanes:EtOAc afforded the title compound as an off-white solid. LC-MS: calculated for C11H8BrN 234.09, observed m/e 236.5 (M+H)+ (Rt 1.72 min).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and water
  4. washThe organic phase was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cd6cd70c2af4aa6b37a2b1e49358f1f
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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