p-Toluenesulfonic acid → 1-(2-bromo-pyridin-4-yl)-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 453064ノート

反応式

HRID 453064 の反応式
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=2)=[C:6]([NH2:18])[CH:5]=1.[CH:20](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([Br:17])[CH:12]=3)[CH:20]=[N:18][C:6]=2[CH:5]=1)=[O:19]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 866585853-Amino-4-(2-bromopyridin-4-ylamino)benzoic acid methyl ester

生成物 1

HCID 866585861-(2-bromo-pyridin-4-yl)-1H-benzoimidazole-5-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

3-Amino-4-(2-bromo-pyridin-4-ylamino)-benzoic acid methyl ester 4 (3 g; 9.3 mmol) was dissolved in 50 ml dry THF and added trimethyl orthoformate (1.4 ml; 13.9 mmol) and p-toluenesulphonic acid (1 g), the reaction mixture was heated to 60° C. for 6 h. LCMS showed almost complete conversion and the reaction was quenched with sodium bicarbonate and extracted with EtOAc (500 ml*3). The organic layer was washed with water and brine. Finally it was dried over sodium sulphate and concentrated in vacuo to give the expected product 5. The compound was pure enough for progress into the next step as seen by NMR and HPLC.

後処理

  1. customthe reaction was quenched with sodium bicarbonate
  2. extractionextracted with EtOAc (500 ml*3)
  3. washThe organic layer was washed with water and brine
  4. dry with materialFinally it was dried over sodium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-da172db2096d4939ba61493dbfbbdb92
出典データセット
uspto-grants-2013_07
特許番号
US08492408B2

反応ノート

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