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

HRID 1028066ノート

反応式

HRID 1028066 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21863594Toluene ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-240face549054277bf8b01839b413245
出典データセット
uspto-grants-2014_05
特許番号
US08735424B2

反応ノート

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