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Water → 4-(2,3-Dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

HRID 2175236
ノート
印刷プレビュー

反応式

HRID 2175236 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12](=[O:25])[CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=1[CH3:24].[OH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:24][C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][CH2:15][CH2:14][CH2:13][C:12]([N:7]1[C:8]2[C:3](=[C:2]([C:31]3[CH:32]=[CH:33][C:28]([CH2:27][OH:26])=[CH:29][CH:30]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:5][CH2:6]1)=[O:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 709817961-(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one

生成物 1

HCID 709818684-(2,3-Dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one収率 93.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a degassed solution of 1-(5-bromo-3,4-dihydroquinolin-1(2H)-yl)-4-(2,3-dimethylphenoxy)butan-1-one (0.216 g, 0.537 mmol), 4-(hydroxymethyl)phenylboronic acid (0.122 g, 0.805 mmol) and potassium carbonate (0.223 g, 1.611 mmol) in dioxane (3.00 mL)/water (1.20 mL) was added tetrakis(triphenylphosphine)palladium (0.016 g, 0.013 mmol). Upon completion of addition, the vial was purged with argon, sealed and stirred at 90° C. for 16 h. After this time, the reaction mixture was partitioned between water and EtOAc, and the organic layer was separated. The aqueous phase was extracted with EtOAc and the combined organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo to provide the crude material. The crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes) to afford the title compound (0.215 g, 93% yield) as a clear colorless oil. LCMS, [M+H]+=430.2.

後処理

  1. additionUpon completion of addition
  2. customthe vial was purged with argon
  3. customsealed
  4. customAfter this time, the reaction mixture was partitioned between water and EtOAc
  5. customthe organic layer was separated
  6. extractionThe aqueous phase was extracted with EtOAc
  7. dry with materialthe combined organic layer was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide the crude material
  11. customThe crude material was purified by flash chromatography (0-50% ethyl acetate:hexanes)

出典と根拠

ORDレコード
ord-e62fb0f7046d4918a8dd6b9ce2baf5e7
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062028B2

反応ノート

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