Potassium Carbonate → 2-(4-Fluorophenethyl)-6-phenylpyridazin-3(2H)-one

HRID 1878762ノート

反応式

HRID 1878762 の反応式
[C:1]1([C:7]2[CH:8]=[CH:9][C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][CH2:15][N:11]2[C:10](=[O:13])[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12]2)=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 751063-Phenyl-6-pyridazoneHCID 5731534-Fluorophenethyl bromide

生成物 1

HCID 598431152-(4-Fluorophenethyl)-6-phenylpyridazin-3(2H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
23 °C

実験手順

A mixture of 6-phenyl-3(2h)-pyridazinone (306 mg, 1.78 mmol), 1-(2-bromo-ethyl)-4-fluoro-benzene (397 μl, 1.95 mmol), and potassium carbonate, −325 mesh (614 mg, 4.44 μmol) in DMF (5 mL) was stirred for 3 days at 23° C. The mixture was partitioned between CH2Cl2 (30 mL) and 5% NaHCO3 (15 mL). The aqueous was further extracted with CH2Cl2 (2×5 mL) and the combined organics was dried over MgSO4, and concentrated under reduced pressure To give a clear oil. MS (ESI pos. ion) m/z (MH+): 295. Calc'd exact mass for C18H15FN2O: 294. 1H NMR (400 MHz, Chloroform-d) δ ppm 3.16 (t, J=7.53 Hz, 2 H) 4.47 (t, J=7.78 Hz, 2 H) 6.88-7.06 (m, 3 H) 7.15-7.25 (m, 2 H) 7.35-7.53 (m, 3 H) 7.59-7.74 (m, 3 H). 13C NMR (101 MHz, Chloroform-d) δ ppm 32.60, 52.08, 114.07, 114.28, 124.73, 127.81, 128.32, 128.89, 129.01, 129.20, 129.27, 132.63, 132.67, 133.57, 143.32, 158.60, 159.33, 161.76.

後処理

  1. customThe mixture was partitioned between CH2Cl2 (30 mL) and 5% NaHCO3 (15 mL)
  2. extractionThe aqueous was further extracted with CH2Cl2 (2×5 mL)
  3. dry with materialthe combined organics was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customTo give a clear oil

出典と根拠

ORDレコード
ord-8dcec5af33a74aa69994eb2c0834f1c8
出典データセット
uspto-grants-2012_11
特許番号
US08314087B2

反応ノート

読み込み中…