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

HRID 1157397

反応式

HRID 1157397 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0c96d0e31dd549c0bea10d136adc4df8
出典データセット
uspto-grants-2010_10
特許番号
US07807684B2

関連ノート

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