Maleimide → HCID 86753054, compound

HRID 2392697Notes

Reaction equation

HRID 2392697 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:19]1(=O)[NH:23][C:22](=[O:24])[CH:21]=[CH:20]1>FC(F)(F)C(O)=O>[CH:6]1[C:5]2[O:1][C:2]3[C:10]4[NH:11][C:12]5[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=5)[C:18]=4[C:20]4=[CH:21][C:22](=[O:24])[N:23]=[C:19]4[C:3]=3[C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 10935MaleimideHCID 99915851H-Indole, 2-(2-benzofuranyl)-

Product 1

HCID 86753054HCID 86753054, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-(2-benzofuryl)indole 2 (250 mg; 1.0 mmol) and maleimide (110 mg; 1.2 mmol) in trifluoroacetic acid (2 mL) was heated in a sealed reaction vial at 125° C. for 18 h. The solid precipitated was collected, washed with TFA and dried to give 150 mg (48%) of product. Recrystallization (THF) gave a tan solid; mp>300° C., MS (ES+) 312 (M+), 1H NMR (DMSO--d6) δ 4.00 (s, 2H), 4.13 (s, 2H), 7.12 (t, 1H), 7.37 (t, 2H), 7.45 (t, 2H), 7.71 (d, 1H), 7.95 (d, 1H), 8.54 (d, 1H), 10.12 (s, 1H), 11.79 (s, 1H). Anal. calcd for C20 H12N2O2 0.4 H2O; C, 75.18; H, 4.04; N, 8.77. Found: C, 75.29, H, 3.86, N, 8.60.

Workup

  1. customThe solid precipitated
  2. customwas collected
  3. washwashed with TFA
  4. customdried

Sources & evidence

ORD record
ord-756c8ac266e44b8495a68a3a48ac8e98
Source dataset
uspto-grants-1998_09
Patent number
US05801190

Reaction notes

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