Diisopropylethylamine → 4-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline

HRID 1028066노트

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HRID 1028066 반응식
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21](Br)[N:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[C:28]=1B(O)O.C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:28]4[C:27]([F:26])=[CH:32][CH:31]=[CH:30][C:29]=4[F:33])[N:20]=3)[CH:17]=2)[N:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 27343362,6-Difluorophenylboronic acidHCID 583875984-(Benzyloxy)-6-(6-bromopyridin-2-yl)quinoline

생성물 1

HCID 583875674-(Benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline수율 74%

시약·촉매·용매 1

HCID 21863594Toluene ethanol용매

실험 절차

A solution of 4-(benzyloxy)-6-(6-bromopyridin-2-yl)quinoline (1.0 equiv.), 2,6 difluorophenylboronic acid (3.0 equiv.), diisopropylethylamine (3.0 equiv) and tetrakis(triphenylphospine)palladium (0.1 equiv.) in 1:1 toluene/ethanol was heated in a microwave at 120° 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 (60-75 EtOAc/hexanes eluant) to yield 4-(benzyloxy)-6-(6-(2,6-difluorophenyl)pyridin-2-yl)quinoline (74%). LC/MS=425.1 (M+H), LC=3.59 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 (60-75 EtOAc/hexanes eluant)

출처 및 근거

ORD 기록
ord-240face549054277bf8b01839b413245
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735424B2

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