Methyl iodide → Tert-butyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]-1-methyl-1H-benzo[d]imidazol-2-yl}piperidine-1-carboxylate

HRID 710117노트

반응식

HRID 710117 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:33]=[CH:32][C:15]2[NH:16][C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:18][C:14]=2[CH:13]=1.[H-].[Na+].CI.[CH3:38]COC(C)=O.O>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:33]=[CH:32][C:15]2[N:16]([CH3:38])[C:17]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH2:20]3)=[N:18][C:14]=2[CH:13]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22728543Water ethylacetateHCID 178451785HCID 178451785, 화합물

생성물 1

HCID 71114581Tert-butyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]-1-methyl-1H-benzo[d]imidazol-2-yl}piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Tert-butyl 4-{5-[2-fluoro-4-(methylsulfonyl)phenyl]-1H-benzo[d]imidazol-2-yl}piperidine-1-carboxylate (85 mg, 0.17 mmol) dissolved in THF (15 ml) and cooled to 0° C. Sodium hydride (9 mg, 0.342 mmol) added to the above mixture and stirred at the same temperature for 30 mins. To this mixture methyl iodide (48 mg, 0.342 mmol) added at same temperature and stirred the reaction mixture at rt for 3 h. Reaction mixture diluted with ice and worked up (EtOAc/H2O). Crude was purified by column chromatography on 60-120 mesh silica gel using EtOAc:Petether (3:1) as eluent to afford the title compound (50 mg) as an orange solid. M.P.: 85-88° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): 7.85-7.75 (m, 2H), 7.73-7.64 (m, 2H), 7.56-7.51 (m, 1H), 7.50-7.45 (m, 1H), 4.39-4.21 (m, 2H), 3.82 (s, 3H), 3.11 (s, 3H), 3.10-3.00 (m, 2H), 3.00-2.88 (m, 2H), 2.05-1.93 (m, 3H), 1.48 (s, 9H).

후처리

  1. stirringstirred the reaction mixture at rt for 3 h
  2. customReaction mixture
  3. additiondiluted with ice
  4. customCrude was purified by column chromatography on 60-120 mesh silica gel

출처 및 근거

ORD 기록
ord-44f72d6a54d74c3ba456d622c8321d21
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181214B2

반응 노트

불러오는 중…