Sodium Carbonate → HCID 58094732, compound

HRID 2282153Notes

Reaction equation

HRID 2282153 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([NH2:9])=[O:8])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:3]=1[C:18]#[N:19].[I-].F[P-](F)(F)(F)(F)F.[CH2:28]([O+](CC)CC)[CH3:29].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Br:1][C:2]1[S:6][C:5]([C:7](=[NH:9])[O:8][CH2:28][CH3:29])=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:3]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 30165Iodide IonHCID 167684Oxonium, triethyl-, hexafluorophosphate(1-) (1:1)HCID 58095225HCID 58095225, compound

Product 1

HCID 58094732HCID 58094732, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-4-cyano-3-(2,4-dichlorophenyl)thiophene-2-carboxamide (prepared in an analogous way to the iodide intermediate shown in Example 3-A; 0.500 g, 1.33 mmol) in dichloromethane (28 mL) at 0° C. was added triethyloxonium hexafluorophosphate (2.31 g, 9.31 mmol). The mixture was allowed to slowly warm to room temperature, and stirred for 16 hours. The solution was poured into 1M sodium carbonate solution at 0° C., then the layers were separated, and the aqueous layer was extracted 3 times with dichloromethane. The organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (0.558 g, 104%). LCMS: (FA) ES+, 405. 1H NMR (400 MHz, d1-chloroform) δ: 7.60-7.57 (m, 1H), 7.43-7.38 (m, 1H), 7.29-7.25 (m, 1H), 4.30-4.22 (m, 2H), 1.40-1.37 (m, 3H).

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted 3 times with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b010df1031f046d893b50f54b7847549
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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