Sodium Carbonate → Bis(2-hydroxy-3,5-dimethylphenyl)-2,2'-bipyridine

HRID 1263570ノート

反応式

HRID 1263570 の反応式
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1B(O)O.Br[C:14]1(Br)[NH:19][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:17][CH:16]=[CH:15]1.[C:27](=[O:30])([O-])[O-].[Na+].[Na+]>COCCOC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[C:16]1[CH:15]=[CH:14][N:19]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[C:17]=1[C:7]1[CH:6]=[C:5]([CH3:9])[CH:4]=[C:3]([CH3:2])[C:27]=1[OH:30]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 18617001(2-Hydroxy-3,5-dimethylphenyl)boronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

生成物 1

HCID 136082253Bis(2-hydroxy-3,5-dimethylphenyl)-2,2'-bipyridine収率 68%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

bis(2-Hydroxy-3,5-dimethylphenyl)-2,2′-bipyridine was prepared by reaction of 2-hydroxy-3,5-dimethylphenylboronic acid (321 mg, 1.92 mmol) with 6,6-dibromo-2,2′-bipyridyl (260 mg, 0.82 mmol), sodium carbonate (2N solution, 2 ml) and tetrakis(triphenylphosphine) palladium (20 mg) in ethylene glycol dimethyl ether (8 ml) at reflux under nitrogen for 88 hours. The solid was filtered from the cooled reaction and washed with acetone and water to give the desired product as a yellow solid (220 mg, 68%); δH [2H6]-DMSO 8.39,(2H, d), 8.31,(2H, t), 8.10,(2H, d), 7.78,(2H, s), 7.10,(2H, s), 2.31,(6H, s), 2.24,(6H, s).

後処理

  1. temperatureat reflux under nitrogen for 88 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with acetone and water

出典と根拠

ORDレコード
ord-463c3a3e766347409bbfe81bdf164e2d
出典データセット
uspto-grants-2003_04
特許番号
US06541490B1

反応ノート

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