Triethylamine → HCID 15513658, compound

HRID 1976724Notes

Reaction equation

HRID 1976724 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](Cl)=[O:16])=[CH:3]1.Cl.C([O:23][C:24](=[NH:38])[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=2)[N:28]([CH3:37])[CH:27]=1)(C)C.CCN(CC)CC>C(Cl)Cl>[CH3:36][O:35][C:31]1[CH:30]=[C:29]2[C:34]([C:26]([C:25]3[C:24](=[O:23])[NH:38][C:15](=[O:16])[C:14]=3[C:4]3[C:5]4[C:10](=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=4)[N:2]([CH3:1])[CH:3]=3)=[CH:27][N:28]2[CH3:37])=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15458808HCID 15458808, compoundHCID 70112506HCID 70112506, compound

Product 1

HCID 15513658HCID 15513658, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of (1-methyl-6-nitro-1H-indol-3-yl)-oxo-acetyl chloride (251 mg, 0.94 mm) and 2-(6-methoxy-1-methyl-1H-indol-3-yl)-acetimidic acid isopropyl ester hydrochloride (280 mg, 0.94 mm) in CH2Cl2(25 mL) was cooled to 0° C., treated with Et3N (0.53 mL, 3.7 mm), and stirred at room temperature while allowing to warm to room temperature overnight. The mixture was then diluted with CH2Cl2 (25 mL), washed with H2O (20 mL), and 0.5 N HCl (20 mL). The combined organic layers were dried over MgSO4, filtered and evaporated. The residue was then combined with toluene (4 mL), cooled to 0° C., treated with pTsOH (197 mg, 1 mm), and stirred for 3 hours. The red solids which precipitated were collected and partitioned between CH2Cl2 (50 mL), and H2O (25 mL). The organic fraction was washed with saturated NaHCO3 solution (25 mL), then dried over MgSO4, filtered and evaporated. Rinsing the residue with tetrahydrofuran (THF) afforded 3-(6-methoxy-1-methyl-1H-indol-3-yl)-4-(1-methyl-6-nitro-1H-indol-3yl)-pyrrole-2,5-dione; mp=308-310° C.; in 31% yield.

Workup

  1. temperatureto warm to room temperature overnight
  2. washwashed with H2O (20 mL), and 0.5 N HCl (20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. temperaturecooled to 0° C.
  7. additiontreated with pTsOH (197 mg, 1 mm)
  8. stirringstirred for 3 hours
  9. customThe red solids which precipitated
  10. customwere collected
  11. custompartitioned between CH2Cl2 (50 mL), and H2O (25 mL)
  12. washThe organic fraction was washed with saturated NaHCO3 solution (25 mL)
  13. dry with materialdried over MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. washRinsing the residue with tetrahydrofuran (THF)

Sources & evidence

ORD record
ord-fbcf18f5c2a94ff8b9a9b18a789c58e6
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

Loading…