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

HRID 1831934노트

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HRID 1831934 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6a90df1ad68d4aac996e1cdc7895a58c
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067540B2

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