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

HRID 392508

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

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—Hs 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); δH (CDCl3) 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.

Workup

customevaporated to dryness
customThe product was chromatographed on silica gel

Sources & evidence

ORD record: ord-549e781af6c34b269a52db529adf544e
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06800636B2

Linked notes

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