Triethylamine → 3-bromo-5-(3-chloro-5-methoxyphenoxy)Pyridine

HRID 1157397Notes

Reaction equation

HRID 1157397 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[Br:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[N:16][CH:17]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14]([O:10][C:4]2[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1033393-Chloro-5-methoxyphenolHCID 38148115-Bromopyridine-3-boronic acid

Product 1

HCID 574436073-bromo-5-(3-chloro-5-methoxyphenoxy)Pyridine

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 372 mg (2.346 mmol) of 3-chloro-5-methoxyphenol (B-1), 947 mg (4.692 mmol) of 5-bromopyridine-3-boronic acid (13-1), 426 mg (2.346 mmol) of copper (II) acetate and 4.0 g of freshly activated powdered 4A molecular sieves was stirred in 20 mL of DCM in a screw top glass sealed tube. The reaction was then treated with 1.635 mL (11.73 mmol) of triethylamine and the vessel was loosely capped. The mixture was vigorously stirred at room temperature for 48 hours. The mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to a black residue. The residue was purified on a CombiFlash silica column eluted with an ethyl acetate:hexanes gradient to give the desired product 13-2 as an oil (Rf=0.7, EtOAc:hexanes 1:4). MS: M+1=314. 1H NMR(CDCl3): 3.79 (s, 3H), 6.47 (m, 1H), 6.61 (m, 1H), 6.74 (m, 1H), 7.46 (m, 1H), 8.33 (d, 1H), 8.46 (d, 1H).

Workup

  1. customsealed tube
  2. customthe vessel was loosely capped
  3. filtrationThe mixture was filtered through a pad of celite
  4. concentrationthe filtrate was concentrated in vacuo to a black residue
  5. customThe residue was purified on a CombiFlash silica column
  6. washeluted with an ethyl acetate

Sources & evidence

ORD record
ord-0c96d0e31dd549c0bea10d136adc4df8
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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