Acetonitrile → HCID 12148999, compound

HRID 1835917Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[C:15]([OH:20])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9].[C:21](#[N:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].ICC#N>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[C:15]([O:20][CH2:22][C:21]#[N:23])[CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1)(=[O:9])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A 50 mL round-bottomed flask equipped with a magnetic stirrer was charged with 1-(2-fluorobenzenesulfonyl)-4-hydroxy-1H-indole (0.600 g, 0.002 mol), 25 mL of anhydrous acetonitrile and potassium carbonate (1.104 g, 0.008 mol). The reaction mixture was cooled to 0° C. and iodoacetonitrile (0.500 g, 0.003 mol) was added dropwise over five minutes. The reaction mixture was allowed to warm to ambient temperature and stirred for eighteen hours. The mixture was taken in ether (200 mL), washed with water (2×30 mL) and brine (1×30 mL), dried over MgSO4 and concentrated in vacuo. The resulting oily brown residue was purified by flash chromatography (8:2 ethyl acetate/hexanes) to give [1-(2-fluoro-benzenesulfonyl)-1H-indol-4-yloxy]acetonitrile as a crystalline solid (0.507 g, 77%). 1H NMR (300 MHz, CDCl3) δ: 4.87 (s, 2 H), 6.76 (d, 1 H, J=13.18), 6.77 (d, 1 H, J=1.51), 7.11 (dt, 1 H, J=8.29, J=1.13), 7.23 (t, 1 H, J=8.29), 7.29 (dt, 1 H, J=7.73, J=1.13), 758 (m, 4 H), 8.03 (m, 1 H).

Workup

customA 50 mL round-bottomed flask equipped with a magnetic stirrer
temperatureto warm to ambient temperature
washwashed with water (2×30 mL) and brine (1×30 mL)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe resulting oily brown residue was purified by flash chromatography (8:2 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7a06b8193225472c9e60aa2d9d041c7e
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774241B2

Reaction notes

Loading…