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

HRID 453064노트

반응식

HRID 453064 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-da172db2096d4939ba61493dbfbbdb92
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492408B2

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