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

HRID 566913노트

반응식

HRID 566913 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-229a93abe6964ab686c0d9b5015a1078
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177419B1

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