2-(1-methyl-1H-indol-7-yl)acetamide → 3-(6-Benzyloxy-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

HRID 2215778

Reaction equation

HRID 2215778 reaction equation
CO[C:3](=[O:23])[C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[NH:8][CH:7]=1)=O.[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][C:32]=2[CH2:34][C:35]([NH2:37])=[O:36])[CH:27]=[CH:26]1.C(O[K])(C)(C)C>C1COCC1>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([C:4]3[C:3](=[O:23])[NH:37][C:35](=[O:36])[C:34]=3[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]4[C:33]=3[N:25]([CH3:24])[CH:26]=[CH:27]4)=[CH:7][NH:8]2)=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 114353972-(1-methyl-1H-indol-7-yl)acetamideHCID 34181007(6-Benzyloxy-1H-indol-3-yl)-oxo-acetic acid methyl esterHCID 178418922HCID 178418922, compound

Product 1

HCID 219500803-(6-Benzyloxy-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dioneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of (6-benzyloxy-1H-indol-3-yl}-oxo-acetic acid methyl ester (1.0 g, 3.2 mmol) and 2-(1-methyl-1H-indol-7-yl)-acetamide (608 mg, 3.2 mmol) in 15 ml THF was added 3.5 equiv. of tBuOK in THF at 0° C. (11.3 ml of 1.0 M solution in THF) under N2. The mixture was stirred at r.t overnight, quenched with conc. HCl 5.0 ml, and neutralized with 5 N NaOH to PH=8. The mixture was extracted with ethyl acetate, and the extract was washed with saturated NaHCO3, brine and water, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by flash chromatography with Hexane:Ethyl acetate (1:1) to yield the title compound (700 mg) as orange solid, 74% yield. MS(m/z): 448.2 (M++1), 446.1 (M−−1); 1HNMR (DMSO-d6) 11.62 (s, 1H), 11.07 (s, 1H), 7.77 (d, J=1.80 Hz, 1H), 7.57 (m, 1H ), 7.26 (m, 5H), 7.21 (d, J=2.40 Hz, 1H), 6.94 (tri, J=6.00 Hz, 1H), 6.84 (m, 2H), 6.44(d, J=2.40 Hz, 1H), 6.16 (s, 1H), 4.97 (s, 2H), 3.62 (s, 3H).

Workup

  1. customquenched with conc. HCl 5.0 ml
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated NaHCO3, brine and water
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography with Hexane:Ethyl acetate (1:1)

Sources & evidence

ORD record
ord-e4bbb6fa380443e0aca38ac8e82bab94
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Linked notes

Loading…