Potassium Carbonate → 4-[(4-fluorobenzyl)oxy]-1-{4-[(1E)-3-hydroxy-1-propen-1-yl]phenyl}pyridin-2(1H)-one

HRID 254409

反応式

HRID 254409 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[CH2:26][OH:27])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].O.N>C(OCC)(=O)C.CN(C=O)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[CH2:26][OH:27])=[CH:20][CH:19]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 11183465(2E)-3-(4-bromophenyl)prop-2-en-1-olHCID 12896473Azane;hydrateHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-one

生成物 1

HCID 668728494-[(4-fluorobenzyl)oxy]-1-{4-[(1E)-3-hydroxy-1-propen-1-yl]phenyl}pyridin-2(1H)-one収率 50.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
155 °C

実験手順

A mixture of 4-[(4-fluorobenzyl)oxy]pyridin-2(1H)-one (1.10 g, 5.0 mmol), (2E)-3-(4-bromophenyl)-2-propen-1-ol (1.28 g, 6 mmol), cuprous iodide (476 mg, 3 mmol), potassium carbonate (829 mg, 6 mmol) and DMF (20 mL) was stirred overnight at 155° C. The reaction liquid was cooled to room temperature, then poured into ammonia water, and ethyl acetate was added for extraction. The organic layer was washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, followed by purification by flash column chromatography (KP-Sil, hexane:ethyl acetate=1:1 to 0:1) to obtain the entitled compound (881 mg).

後処理

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. additionwas added for extraction
  4. washThe organic layer was washed with water and saturated saline
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. customfollowed by purification by flash column chromatography (KP-Sil, hexane:ethyl acetate=1:1 to 0:1)

出典と根拠

ORDレコード
ord-d8bc3e29064449df8c43fa1906e3655b
出典データセット
uspto-grants-2011_01
特許番号
US07875633B2

関連ノート

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