Benzimidazole → 2-benzimidazol-1-yl-N-(4-bromophenyl)-acetamide

HRID 1455616노트

반응식

HRID 1455616 반응식
Br[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[O:4].[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:13]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=2)=[O:4])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]=[CH:14]1

참가 물질

5

반응물 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 2255262-Bromo-n-(4-bromophenyl)acetamide

생성물 1

HCID 170284752-benzimidazol-1-yl-N-(4-bromophenyl)-acetamide수율 63.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2-Bromo-N-(4-bromophenyl)-acetamide (3.083 g, 10.522 mmol), prepared according to J. Med. Chem., 1996, 4(2), 197-203, benzimidazole (1.24 g, 10.52 mmol) and K2CO3 were combined and dissolved in DMF (60 mL) under nitrogen. The reaction mixture was stirred at room temperature overnight before filtering and purifing by SCX cartridge. The crude product thus obtained was washed with EtOAc to remove excess benzimidazole, yielding the pure product (2.20 g, 63% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 5.17 (2H, s), 7.19-7.28 (2H, m), 7.51 (2H, d, J=12 Hz), 7.51-7.56 (1H, m), 7.57 (2H, d, J=12 Hz), 7.66 (1H, d, J=8 Hz), 8.22 (1H, s), 10.57 (1H, s). MS (ES) m/z: 332.5 [M+H].

후처리

  1. filtrationbefore filtering
  2. customThe crude product thus obtained
  3. washwas washed with EtOAc
  4. customto remove excess benzimidazole

출처 및 근거

ORD 기록
ord-63ee8bd55d7d41fba75081141da18398
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482469B2

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