Acetic Acid → 4-Bromo-3-((dimethylamino)methyl)-1H-indole-7-carboxamide

HRID 2361433Notes

Reaction equation

HRID 2361433 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH2:18]=O.[CH3:20][NH:21][CH3:22]>C(O)C>[Br:5][C:6]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:7]=1[C:8]([CH2:20][N:21]([CH3:18])[CH3:22])=[CH:9][NH:10]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 497579964-Bromo-1H-indole-7-carboxamide

Product 1

HCID 679948144-Bromo-3-((dimethylamino)methyl)-1H-indole-7-carboxamideYield 109.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Acetic acid (1.15 mL, 20.08 mmol) was added to a suspension of 4-bromo-1H-indole-7-carboxamide (3 g, 12.55 mmol), paraformaldehyde (0.603 g, 20.08 mmol) and dimethylamine (2 M in methanol, 10 mL, 20.08 mmol) in ethanol (50 mL). The mixture was heated to 80° C. After 2 h, the ethanol was removed under vacuum. The residue was partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine (15 mL), dried and concentrated to afford the crude desired product as a light brown solid (4.08 g). LCMS (M+H)+ m/z 295.8, 297.8.

Workup

  1. customthe ethanol was removed under vacuum
  2. customThe residue was partitioned between NaHCO3 (aq) and EtOAc
  3. washThe organic phase was washed with brine (15 mL)
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-203baf78fd574db695a788f10ed25d6c
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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