Sodium Carbonate → 3-Bromo-5-(4-methoxyphenyl)pyridine

HRID 1878614ノート

反応式

HRID 1878614 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N.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:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:14]2[CH:15]=[CH:16][C:11]([O:10][CH3:9])=[CH:12][CH:13]=2)[CH:7]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 693693,5-DibromopyridineHCID 201262(4-Methoxyphenyl)boronic acid

生成物 1

HCID 120670673-Bromo-5-(4-methoxyphenyl)pyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 3,5-dibromopyridine (Sigma-Aldrich, St. Louis, USA) (1 eq, 8.4 mmol, 2 g) and 4-methoxy-phenylboronic acid (Sigma-Aldrich, St. Louis, USA) (1 eq, 8.4 mmol, 1.30 g) in MeCN (12 ml), Na2CO3 (2 eq, 16.7 mmol, 1.79 g) and Pd(PPh3)4 (0.04 eq, 0.334 mmol, 398 mg) are added. The mixture is heated using microwave radiation at 140° C. for 10 min. The solvents are evaporated, the residue is taken up in aqueous NaOH solution (1 M) and extracted with DCM. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (hexane/EtOAc) yields the title compound; [M+H]+=264/266.

後処理

  1. temperatureThe mixture is heated
  2. customat 140° C.
  3. customfor 10 min
  4. customThe solvents are evaporated
  5. extractionextracted with DCM
  6. washThe organic layer is washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-9851ea1746594511a32cc08516254079
出典データセット
uspto-grants-2012_11
特許番号
US08314112B2

反応ノート

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