Sodium Carbonate → HCID 58094732, compound

HRID 2402479Notes

Reaction equation

HRID 2402479 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-77b4a03264c74b9caf21fb423e43fab2
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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