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

HRID 1263570노트

반응식

HRID 1263570 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-463c3a3e766347409bbfe81bdf164e2d
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541490B1

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