Formamide → HCID 178497210, compound

HRID 930189Notes

Reaction equation

HRID 930189 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11](OCC)=[O:12])=[CH:8][CH:7]=[C:6]([C:16]([O:18][CH3:19])=[O:17])[CH:5]=2.C([O-])=O.[NH4+].[CH:24]([NH2:26])=O>O>[OH:12][C:11]1[C:10]2[C:9]3[C:4](=[CH:5][C:6]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][CH:8]=3)[NH:3][C:2]=2[N:1]=[CH:24][N:26]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 59447961HCID 59447961, compound

Product 1

HCID 178497210HCID 178497210, compoundYield 107.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

In a 100 mL round-bottom flask were added 3-ethyl 6-methyl 2-amino-1H-indole-3,6-dicarboxylate (1.1 g, 4.19 mmol), ammonium formate (0.53 g, 8.39 mmol), and formamide (16.7 mL, 419 mmol) to give a tan suspension which was heated to 165° C. for 12 hours. The mixture was allowed to cool to room temperature and water was added. The resulting precipitate was filtered, air-dried and dried under high vacuum overnight to afford 1.1 g of the title compound. LCMS m/z 244.2 (M+H)+, retention time (on analytical HPLC)=1.51 minutes.

Workup

  1. customto give a tan suspension which
  2. temperatureto cool to room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customair-dried
  5. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-cedcbe7939b8407ca75aae2f9a7ed1f4
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

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