Potassium Carbonate → 7-(1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

HRID 241975ノート

反応式

HRID 241975 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[O:15][N:14]=[C:13]([NH2:17])[C:12]=3[CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]2[N:18]([CH3:21])[N:19]=[CH:20][C:3]=12.[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:21][N:18]1[C:4]2=[N:5][C:6]([C:8]3[C:16]4[O:15][N:14]=[C:13]([NH2:17])[C:12]=4[CH:11]=[CH:10][CH:9]=3)=[CH:7][C:2]([O:32][C:29]3[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=3)=[C:3]2[CH:20]=[N:19]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 580832327-(4-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine

生成物 1

HCID 462186757-(1-methyl-4-(4-(methylsulfonyl)phenoxy)-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine収率 21.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
155 °C

実験手順

A mixture of 7-(4-chloro-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)benzo[d]isoxazol-3-amine 17 (0.032 g, 0.106 mmol), 4-methylsulfonyl phenol 8a (0.036 g, 0.213 mmol) and potassium carbonate (0.15 g, 1.06 mmol) in 2 mL DMF was heated in a microwave at 155° C. for 30 minutes. The reaction mixture was filtered, solvent removed and diluted with ethyl acetate. The organic portions were pooled and washed with saturated bicarbonate solution and brine, dried over anhydrous sodium sulfate and solvent was removed. The crude material was purified using mass directed purification to give 10 mg of 121. 1H NMR (400 MHz, DMSO) δ=8.02-7.58 (m, 8H), 7.58 (dd, J=26.9, 35.7, 2H), 6.53 (s, 1H), 4.15-4.01 (m, 3H), 3.3-3.06 (m, 3H). MS (ESI) m/z 436.0 (M+1)+

後処理

  1. filtrationThe reaction mixture was filtered
  2. customsolvent removed
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate and solvent
  6. customwas removed
  7. customThe crude material was purified
  8. custompurification

出典と根拠

ORDレコード
ord-0b0a05b0f91f416e8cc17654c2d7f672
出典データセット
uspto-grants-2014_02
特許番号
US08653098B2

反応ノート

読み込み中…