6-(Methanesulfonyloxymethyl)quinoline → 6-[(1H-Imidazol-1-YL)methyl]quinoline

HRID 279237

반응식

HRID 279237 반응식
CS(O[CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2)(=O)=O.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.[Na]>CN(C=O)C>[N:17]1([CH2:6][C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[N:13]=[CH:12][CH:11]=[CH:10]3)[CH:21]=[CH:20][N:19]=[CH:18]1

참가 물질

4

반응물 2

HCID 226628996-(Methanesulfonyloxymethyl)quinolineHCID 57373095Imidazole sodium

생성물 1

HCID 199671066-[(1H-Imidazol-1-YL)methyl]quinoline수율 27%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

The title product from Step A above was dissolved in anhydrous DMF (10 mL) and sodium imidazole (0.367 g, 4.08 mmoles) was added. The mixture was heated at 70° C. under argon for 2 h and then evaporated to dryness. The product was chromatographed on silica gel to give the title compound (0. 1559 g, 27%): FABMS: m/z 210.0 (MH+); δH (CDCl3) 5.34 (1H, s, CH2), 6.97 (1H, s, Im-H5), 7.15 (1H, s, Im-H4), 7.44 (1H, dd, Ar—H3), 7.52 (2H, m, Ar—H5 and Ar—H7), 7.64 (1H, s, Im-H2), 8.12 (2H, d, Ar—H4 and Ar—H8) and 8.95 ppm (1H, d, Ar—H2); δC (CDCI3) CH2: 50.6; CH: 119.4, 121.8, 125.9, 128.4, 130.1, 130.5, 136.0, 137.6, 151.0; C: 128.2, 134.6, 147.9.

후처리

  1. customevaporated to dryness
  2. customThe product was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-0535344dc4404caabe1c0efd09357d28
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362188B1

연결된 노트

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