Sodium Carbonate → HCID 67424558, compound

HRID 1910355Notes

Reaction equation

HRID 1910355 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.O.C(COC)OC>[C:9]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=2)[CH:10]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 693532,5-DibromopyridineHCID 2734315(3-Phenylphenyl)boronic acid

Product 1

HCID 67424558HCID 67424558, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 1000 mL, 3-necked flask equipped with a stir bar, nitrogen inlet, and a reflux condenser were added 2,5-dibromopyridine (39.9 g, 84.2 mmol), 3-biphenylboronic acid (20.0 g, 101 mmol), palladium(H) acetate (0.47 g, 2.1 mmol), triphenylphosphine (2.2 g, 8.4 mmol), sodium carbonate (24.1 g, 227 mmol), dimethoxyethane (170 mL), and water (114 mL). The reaction mixture was heated at reflux for 16 h, after which ethyl acetate (200 mL) was added. The organic layer was then dried over magnesium sulfate and evaporated to dryness. Purification of the resulting solid on a silica gel column with ethyl acetate/hexane as the eluent yielded 19.0 g (73%) of 2-(biphenyl-3-yl)-5-bromopyridine as a white solid.

Workup

  1. customTo a 1000 mL, 3-necked flask equipped with a stir bar, nitrogen inlet, and a reflux condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 16 h
  4. dry with materialThe organic layer was then dried over magnesium sulfate
  5. customevaporated to dryness
  6. customPurification of the resulting solid on a silica gel column with ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-0b4d38920fdb4d318a6ee30bc03b37ee
Source dataset
uspto-grants-2013_12
Patent number
US08603645B2

Reaction notes

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