Sodium Carbonate → HCID 58574864, compound

HRID 1619381Notes

Reaction equation

HRID 1619381 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH:9]=[C:10]([C:15]([O:17][CH3:18])=[O:16])[C:11](OC)=[O:12])[CH:3]=1.P(Br)(Br)(Br)=O.C([O-])([O-])=O.[Na+].[Na+]>O>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:11](=[O:12])[C:10]([C:15]([O:17][CH3:18])=[O:16])=[CH:9][N:8]=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24613Phosphorus oxybromideHCID 67257898HCID 67257898, compound

Product 1

HCID 58574864HCID 58574864, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of dimethyl 2-((4-bromopyridin-2-ylamino)methylene)malonate (4.8 g, 15.2 mmol, 1 equiv) and POBr3 (16.1 g, 56.1 mmol, 3.7 equiv) was stirred at 80° C. for 2 h. After it was cooled to room temperature, the reaction mixture was poured into water carefully. Then the solution was adjusted pH to 8 with aq. Na2CO3 and extracted with DCM (3×200 mL). The combined organic layers were dried over Na2SO4 and concentrated to give 3.4 g of the desired product. MS (ESI): 283, 285 (MH+).

Workup

  1. temperatureAfter it was cooled to room temperature
  2. extractionextracted with DCM (3×200 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bbee26132a4c480ebd76c09e7dbfd2d4
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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