Triphenylphosphine → Ethyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate

HRID 2423468ノート

反応式

HRID 2423468 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]2.[OH:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O.O1CCOCC1>[OH:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:5]3)=[CH:20][CH:19]=1

参加物

9

反応物 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 27343604-Hydroxyphenylboronic acidHCID 53404703Ethyl 6-bromoquinoline-2-carboxylate

生成物 1

HCID 59321569Ethyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate収率 58.4%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
60 °C

実験手順

Palladium(II)acetate (17.1 mg, 76.0 μmol) was added to ethyl 6-bromo-2-quinolinecarboxylate (426.0 mg, 1.52 mmol, from Example 32c), 4-hydroxy-phenyl-boronic acid (314.6 mg, 2.28 mmol), triphenylphosphine (39.9 mg, 152.1 μmol), and potassium phosphate (1.13 g, 5.32 mmol). Then, dioxane (7.6 mL) was added to the mixture, followed by water (152 μL), and the reaction mixture was heated open to the atmosphere at 60° C. in an oil bath for 16 hours, then allowed to cool to room temperature. Water was added followed by ethyl acetate and the mixture was filtered through Celite®. The filtrate was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 2:3 ethyl acetate:hexanes to give 260.5 mg (58%) of ethyl 6-(4-hydroxyphenyl)-2-quinolinecarboxylate as a solid. 1H NMR (400 MHz, d6-DMSO): δ 9.74 (s, 1H), 8.55 (d, J=9 Hz, 1H), 8.28 (s, 1H), 8.19-8.10 (m, 3H), 7.72 (d, J=9 Hz, 2H), 6.92 (d, J=9 Hz, 2H), 4.42 (q, J=7 Hz, 2H), 1.38 (t, J=7 Hz, 3H). ESI-LCMS m/z 294 (M+H)+.

後処理

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through Celite®
  3. extractionThe filtrate was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 2:3 ethyl acetate

出典と根拠

ORDレコード
ord-da06556032f741faabfe13d9914e742c
出典データセット
uspto-grants-2011_06
特許番号
US07960552B2

反応ノート

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