Sodium Iodide → HCID 71601532, compound

HRID 2284386Notes

Reaction equation

HRID 2284386 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[CH:18]=1)[N:5]([CH2:7][C:8]1[CH:15]=[C:11]2[O:12][CH2:13][CH2:14][N:10]2[N:9]=1)[CH3:6].F[C:21](F)(F)S(OC)(=O)=O.[I-].[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.CC([O-])(C)C.[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]([CH2:7][C:8]2[N:9]([CH3:21])[N:10]([CH:14]=[CH2:13])[C:11](=[O:12])[CH:15]=2)[CH3:6])[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 9526Methyl triflateHCID 23665647Potassium tert-butoxideHCID 71601531HCID 71601531, compound

Product 1

HCID 71601532HCID 71601532, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 36 (200 mg, 0.67 mmol) in anhydrous acetonitrile (6 mL), methyl trifluoromethanesulfonate (85 uL, 0.75 mmol) was added, and the solution was stirred for 2 h before the addition of sodium iodide (195 mg, 1.3 mmol) and TsOH (127 mg, 0.67 mmol). After conversion to the iodinated intermediate by overnight stirring, KOtBu (188 mg, 1.7 mmol) was added to the mixture, which was further stirred for 1 h. After evaporation of the volatiles, the residue was purified on a silica gel column, eluting with a mixture of MeOH and dichloromethane (4% MeOH) to afford 37 as a yellow liquid (115 mg, 55%). 1H NMR (CDCl3, 500 MHz): δ=6.85 (dd, J=9.0, 16.0 Hz, 1H), 6.77 (t, J=1.5 Hz, 2H), 6.56 (d, J=1.5 Hz, 2H), 5.37 (s, 1H), 4.88-4.80 (m, 2H), 4.31 (s, 2H), 3.17 (s, 3H), 2.99 (s, 3H); 13C NMR (CDCl3, 125 MHz): δ=165.4, 159.2, 150.3, 136.0X2, 126.3, 118.0, 111.3X2, 101.1, 99.5, 49.6, 39.0, 37.3 ppm.

Workup

  1. stirringwas further stirred for 1 h
  2. customAfter evaporation of the volatiles
  3. customthe residue was purified on a silica gel column
  4. washeluting with a mixture of MeOH and dichloromethane (4% MeOH)

Sources & evidence

ORD record
ord-53d4f6fc3cd242a2ad0dadeabb90d290
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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