Dimethylformamide → HCID 58437409, compound

HRID 1258180Notes

Reaction equation

HRID 1258180 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:29]=[O:30]>>[CH2:1]([O:8][C:9]([C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH:29]=[O:30])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 10264164Benzyl 1H-indole-5-carboxylate

Product 1

HCID 58437409HCID 58437409, compound

Procedure

To a solution of 1H-indole-5-carboxylic acid benzyl ester (3.5 g) in N,N-dimethylformamide (30 mL) was added phosphoryl chloride (2.6 g) under ice cooling and this mixture was stirred at room temperature for 2 hours. To this reaction mixture was added 2 mol/L aqueous sodium hydroxide solution until the pH became 6 and this mixture was stirred at 70° C. for 30 minutes. After cooling to ambient temperature, the precipitated solid was collected by filtration, and washed with water and methanol, dried to give the title compound (3.9 g).

Workup

  1. stirringthis mixture was stirred at 70° C. for 30 minutes
  2. temperatureAfter cooling to ambient temperature
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water and methanol
  5. customdried

Sources & evidence

ORD record
ord-382b516fe41a4f54bd2ff47b4e79e6f2
Source dataset
uspto-grants-2013_06
Patent number
US08466152B2

Reaction notes

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