Potassium Carbonate → 2,6-Difluoro-3-[3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide

HRID 453100ノート

反応式

HRID 453100 の反応式
Br[CH2:2][C:3]1[S:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:4]=1.[F:16][C:17]1[C:25]([OH:26])=[CH:24][CH:23]=[C:22]([F:27])[C:18]=1[C:19]([NH2:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:16][C:17]1[C:25]([O:26][CH2:2][C:3]2[S:7][N:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[N:4]=2)=[CH:24][CH:23]=[C:22]([F:27])[C:18]=1[C:19]([NH2:21])=[O:20]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 451201362,6-Difluoro-3-hydroxybenzamideHCID 595495215-Bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole

生成物 1

HCID 252311072,6-Difluoro-3-[3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-ylmethoxy]-benzamide収率 30%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

To a solution of 5-bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole (0.048 g, 0.15 mmol) in DMF (2 ml) was added 2,6-difluoro-3-hydroxybenzamide (0.027 g, 0.15 mmol) and potassium carbonate (0.76 g, 0.55 mmol). The reaction mixture was stirred at 25° C. for 12 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was evaporated to dryness under vacuum, added 30 ml water and extracted with ethyl acetate (3×20 ml). The combined organic layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was purified over silica gel (100-200 M, 50% EtOAc-Hexane) to get the desired product (0.011 g, 30%).

後処理

  1. customAfter the completion of the reaction (TLC monitoring)
  2. customthe reaction mixture was evaporated to dryness under vacuum
  3. additionadded 30 ml water
  4. extractionextracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe crude residue was purified over silica gel (100-200 M, 50% EtOAc-Hexane)

出典と根拠

ORDレコード
ord-3e4c7f56f18c4ccb8d3204e62967f375
出典データセット
uspto-grants-2013_07
特許番号
US08492414B2

反応ノート

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