2,6-Dibromopyridine → 4-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline

HRID 1028065노트

반응식

HRID 1028065 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31](Br)[N:30]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:31]3[CH:32]=[CH:33][CH:34]=[C:29]([Br:28])[N:30]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 122742,6-DibromopyridineHCID 583876054-(Benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

생성물 1

HCID 583875984-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline수율 36%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of 4-(benzyloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1.0 equiv.), 2,6 dibromopyridine (1.0 equiv.) and Pd(dppf)Cl2—CH2Cl2 (0.1 equiv.) in 3:1 DME/2M Na2CO3 was heated in a microwave at 100° C. for 20 minutes. Upon cooling, the solution was partitioned between EtOAc and H2O. Upon separation, the organic layer was washed with NaCl(sat.), dried over MgSO4, concentrated and purified by silica gel chromatography (70-90 EtOAc/hexanes eluant) to yield 4-(benzyloxy)-6-(6-bromopyridin-2-yl)quinoline (36%). LC/MS=391.1/393.1 (M+H), LC=3.36 min.

후처리

  1. temperatureUpon cooling
  2. customthe solution was partitioned between EtOAc and H2O
  3. customUpon separation
  4. washthe organic layer was washed with NaCl(sat.)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography (70-90 EtOAc/hexanes eluant)

출처 및 근거

ORD 기록
ord-d06e05df8eb54070b3bb3b6979c81e73
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735424B2

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