Potassium Carbonate → 4-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

HRID 1831934ノート

反応式

HRID 1831934 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 36077244-Benzyloxy-2(1H)-pyridone

生成物 1

HCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one収率 67.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 4-benzyloxy-1H-pyridin-2-one (1.0 g, 5 mmol) and K2CO3 (2.0 g, 9.9 mmol) in DMF (30 mL) was added 3-fluorobenzyl bromide (1.4 g, 7.5 mmol), and the reaction mixture was heated to 110° C. for 3 h. The reaction mixture was cooled to room temperature, and partitioned between EtOAc and water. The organic solution was washed with water and then brine, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography (silica, eluent 97:3 to 93:7 methylene chloride/methanol) afforded 4-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one (1.04 g, 67%): 1H NMR (300 MHz, CDCl3) δ 7.45-7.25 (m, 5H), 7.13 (d, J=8 Hz, 1H), 7.10-6.90 (m, 3H), 6.10-5.95 (m, 2H), 5.07 (s, 2H), 5.00 (s, 2H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic solution was washed with water
  4. dry with materialbrine, dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography (silica, eluent 97:3 to 93:7 methylene chloride/methanol)

出典と根拠

ORDレコード
ord-6a90df1ad68d4aac996e1cdc7895a58c
出典データセット
uspto-grants-2006_06
特許番号
US07067540B2

反応ノート

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