Methyl iodide → HCID 57501702, compound

HRID 601510Notes

Reaction equation

HRID 601510 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:15](=[O:23])[C:16]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].I[CH3:25]>C1COCC1.O>[CH3:25][N:12]1[C:13]2[C:9](=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:14]=2)[C:10]([C:15](=[O:23])[C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:11]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57421475HCID 57421475, compound

Product 1

HCID 57501702HCID 57501702, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add NaH (0.83 g, 20.8 mmol) to a solution of 1-(6-nitro-1H-indol-3-yl)-2-pyrrolidin-1-yl-ethane-1,2-dione (5.0 g, 17.42 mmol) in THF (60 mL). Stir at room temperature for 10 min, add iodomethane (1.18 mL, 19.2 mmol), and continue stirring for 18 h. Dilute with water and extract with EtOAc (2×). Filter the solid that formed between the layers during the extraction. Dry organic portion, concentrate, and combine the solids. Triturate the solid with ether, filter, and dry to obtain the title compound (5.20 g, 99%). 1H NMR (400 MHz, DMSO-d6): δ 8.59 (m, 2H), 8.30 (d, 1H, J=8.8 Hz), 8.17 (dd, 1H, J=8.8, 2.2 Hz), 4.01 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.41 (t, 2H, J=6.4 Hz), 1.85 (m, 4H).

Workup

  1. stirringcontinue stirring for 18 h
  2. extractionextract with EtOAc (2×)
  3. filtrationFilter the solid
  4. customthat formed between the layers during the extraction
  5. concentrationDry organic portion, concentrate
  6. customTriturate the solid with ether
  7. filtrationfilter
  8. customdry

Sources & evidence

ORD record
ord-09313abe047840578dc19e01d2db1db2
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

Loading…