Sodium Carbonate → 6,6'-Bis(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine

HRID 566913ノート

反応式

HRID 566913 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][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[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:22]1[N:21]=[C:20]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([C:7]3[CH:6]=[C:5]([O:8][CH3:9])[CH:4]=[CH:3][C:27]=3[OH:30])[N:19]=2)[CH:25]=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 18617021(2-Hydroxy-5-methoxyphenyl)boronic acidHCID 186170956,6-Dibromo-2,2'-bipyridyl

生成物 1

HCID 1355369316,6'-Bis(2-hydroxy-5-methoxyphenyl)-2,2'-bipyridine収率 44%

試薬・触媒・溶媒 2

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

実験手順

6,6′-Bis(2-hydroxy-5-methoxyphenyl)-2,2′-bipyridine was prepared by reaction of 2-hydroxy-5-methoxyphenylboronic acid (650 mg, 3.87 mmol) with 6,6-dibromo-2,2′-bipyridyl (520 mg, 1.64 mmol), sodium carbonate (2N solution, 4 ml) and tetrakis(triphenylphosphine) palladium (40 mg) in ethylene glycol dimethyl ether (16 ml) at reflux under nitrogen for 11 hours. The solid was filtered from the cooled reaction and washed with ether and water. The residue was dissolved in toluene and filtered through a short column of silica, washing through with further toluene. The combined filtrate and washings were concentrated under vacuum to give the desired product as a yellow solid (286 mg, 44%); δH [2H6]-DMSO 8.30,(2H, d), 8.13,(4H, m), 7.56,(2H, s), 6.88,(4H, m), 3.73,(6H, s).

後処理

  1. temperatureat reflux under nitrogen for 11 hours
  2. filtrationThe solid was filtered from the cooled reaction
  3. washwashed with ether and water
  4. dissolutionThe residue was dissolved in toluene
  5. filtrationfiltered through a short column of silica
  6. washwashing through with further toluene
  7. concentrationThe combined filtrate and washings were concentrated under vacuum

出典と根拠

ORDレコード
ord-229a93abe6964ab686c0d9b5015a1078
出典データセット
uspto-grants-2001_01
特許番号
US06177419B1

反応ノート

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