Borane;tetrahydrofuran → HCID 57421476, compound

HRID 601511Notes

Reaction equation

HRID 601511 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([C:14](=O)[C:15]([N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=O)=[CH:3]1.B.C1COCC1>C1COCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[C:4]([CH2:14][CH2:15][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:3]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 57501702HCID 57501702, compound

Product 1

HCID 57421476HCID 57421476, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 1-(1-methyl-6-nitro-1H-indol-3-yl)-2-pyrrolidin-1-yl-ethane-1,2-dione (5.0 g, 17.4 mmol) in THF (20 mL) with BH3.THF (70 mL of 1N in THF, 70 mmol) and stir at room temperature for 18 h. Concentrate the reaction mixture and add EtOH (100 mL) followed by 5N HCl (20 mL) and reflux for 6 h. Concentrate and dilute with 1N NaOH (100 mL). Extract with CH2Cl2 (2×), then extract with EtOAc (2×). Combine the organics, dry, and concentrate. Purify by flash chromatography using 0-10% 2N NH3/MeOH in CH2Cl2, to give the title compound (2.5 g, 53%). 1H NMR (400 MHz, DMSO-d6): δ 8.26 (d, 1H, J=2.2 Hz), 7.98 (dd, 1H, J=8.8, 1.8 Hz), 7.61 (d, 1H, is J=8.8 Hz), 7.19 (s, 1H), 3.84 (s, 3H), 2.97 (t, 2H, J=8.1 Hz), 2.76 (t, 2H, J=8.1 Hz), 2.61 (m, 4H), 1.83 (m, 4H).

Workup

  1. concentrationConcentrate the reaction mixture
  2. additionadd EtOH (100 mL)
  3. temperaturereflux for 6 h
  4. concentrationConcentrate
  5. additiondilute with 1N NaOH (100 mL)
  6. extractionExtract with CH2Cl2 (2×)
  7. extractionextract with EtOAc (2×)
  8. customCombine the organics, dry
  9. concentrationconcentrate
  10. customPurify by flash chromatography

Sources & evidence

ORD record
ord-2f4fe365f8f74889b75c6101ba36274f
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

Loading…