Potassium Carbonate → N,N-diethyl-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1yl]phenoxyacetamide

HRID 1084837

反応式

HRID 1084837 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH2:24]([N:26]([CH2:31][CH3:32])[C:27](=[O:30])[CH2:28]Br)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:24]([N:26]([CH2:31][CH3:32])[C:27](=[O:30])[CH2:28][O:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([N:10]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9]2)[CH:18]=1)[CH3:25]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 2255452-bromo-N,N-diethylacetamideHCID 147962583-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine

生成物 1

HCID 14796274N,N-diethyl-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1yl]phenoxyacetamide収率 40.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

In 75 ml of dimethylformamide were suspended 5.0 g of 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-1H-pyrazolo[3,4-b]pyridine, 3.5 g of N,N-diethylbromoacetamide and 2.5 g of potassium carbonate. The mixture was stirred at 60° C. for 5 hours. After the solvent was distilled off under reduced pressure, the residue was extracted with ethyl acetate-water. The organic layer was concentrated. Isopropyl ether was added to the residue for crystallization. The obtained crude crystals were recrystallized from ethyl acetate to give 2.8 g of N,N-diethyl-3-[3-(4-fluorophenyl)-1H-pyrazolo[3,4-b]pyridin-1yl]phenoxyacetamide, m.p. 102°-105° C.

後処理

  1. distillationAfter the solvent was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate-water
  3. concentrationThe organic layer was concentrated
  4. additionIsopropyl ether was added to the residue for crystallization
  5. customThe obtained crude crystals
  6. customwere recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-2d06a56142c04d5bbfddb29f84459f6c
出典データセット
uspto-grants-1991_04
特許番号
US05006520

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