Acetonitrile → HCID 58095079, compound

HRID 2402477Notes

Reaction equation

HRID 2402477 reaction equation
[C:1]([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=2)=[C:6]([C:16]#[N:17])[C:5]=1[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])(=[O:3])[CH3:2].OI(C1C=CC=CC=1)[O:28][S:29]([C:32]1[CH:38]=[CH:37][C:35]([CH3:36])=[CH:34][CH:33]=1)(=[O:31])=[O:30].C(#N)C>>[CH3:36][C:35]1[CH:34]=[CH:33][C:32]([S:29]([O:31][CH2:2][C:1]([C:4]2[S:8][C:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([F:15])[CH:10]=3)=[C:6]([C:16]#[N:17])[C:5]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[O:3])(=[O:30])=[O:28])=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 325434[Hydroxy(tosyloxy)iodo]benzeneHCID 58094890HCID 58094890, compound

Product 1

HCID 58095079HCID 58095079, compoundYield 46%

Conditions

Temperature
90 °C

Procedure

A mixture of 5-acetyl-4-(2,4-dichlorophenyl)-2-(2-fluoropyridin-4-yl)thiophene-3-carbonitrile (0.48 g, 1.2 mmol) and [hydroxy(tosyloxy)iodo]benzene (0.819 g, 2.09 mmol) in ACN (20 mL, 400 mmol) was heated at 90° C. overnight. The mixture was cooled down to rt. The solvent was evaporated and the residue was purified by column chromatography to afford the title compound (0.31 g, 45%). 1H NMR (300 MHz, d1-chloroform) δ: 8.44 (1H, d, J=5.27 Hz), 7.69 (2H, d, J=8.34 Hz), 7.62 (2H, ddd, J=6.91, 3.43, 1.72 Hz), 7.47 (1H, dd, J=8.25, 2.02 Hz), 7.39-7.33 (3H, m), 7.30 (1H, d J=5.79), 4.47 (2H, s), 2.47 (3H, s)

Workup

  1. temperatureThe mixture was cooled down to rt
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b76e7a1e4cd34f43981b79b81cc68a78
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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