Fumaric Acid → 5-bromo-3-{[(2S)-1-methylpyrrolidin-2-yl]methyl}-1H-indole (2E) but-2-enedioate

HRID 1970088Notes

Reaction equation

HRID 1970088 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH3:25]>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[Br:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]2[CH2:19][C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[CH3:25]

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 25272002(S)-5-Bromo-3-((1-methylpyrrolidin-2-YL)methyl)-1H-indole

Product 1

HCID 673072855-bromo-3-{[(2S)-1-methylpyrrolidin-2-yl]methyl}-1H-indole (2E) but-2-enedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.46 g of fumaric acid were added to a solution of 8.75 g of crude 5-bromo-3-{[(2S)-1-methylpyrrolidin-2-yl]methyl}-1H-indole (HPLC assay 64.9%) in 43.75 mL of ethanol. After stirring for 2 hours the reaction mixture was filtered washing with mL of ethanol/heptane in a 1/1 ratio and the crystal was dried in oven under vacuum until a constant weight of 7.1 g (HPLC purity 91.7%) was obtained.

Workup

  1. filtrationwas filtered
  2. washwashing with mL of ethanol/heptane in a 1/1 ratio
  3. customthe crystal was dried in oven under vacuum until a constant weight of 7.1 g (HPLC purity 91.7%)
  4. customwas obtained

Sources & evidence

ORD record
ord-ed1a0f392ae94a72a6b65faceddb8093
Source dataset
uspto-grants-2013_04
Patent number
US08426612B2

Reaction notes

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