5-Bromoindole → HCID 15326267, compound

HRID 1586044Notes

Reaction equation

HRID 1586044 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][N:12]1[C:16](=[O:17])[CH:15]=[CH:14][C:13]1=[O:18]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:15]1[C:16](=[O:17])[N:12]([CH3:11])[C:13](=[O:18])[CH2:14]1

Participants

4

Reactant 2

HCID 249055-BromoindoleHCID 70261N-Methylmaleimide

Product 1

HCID 15326267HCID 15326267, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 5-bromoindole (4.00 g, 20.40 mmol) and N-methylmaleimide (5.00 g, 45.00 mmol, 2.2 eq) in glacial acetic acid (50 mL) was heated at reflux under nitrogen for 120 hours. The resulting reaction mixture was evaporated under reduced pressure, and the residue was stirred vigorously in a solution of ether/methylene chloride (9:1, 200 mL) for 2 hours. Undissolved solid was filtered to afford the title compound (4.34 g, 14.13 mmol, 69%) as a pale yellow solid: mp, 196.0-197.0° C.; TLC Rf =0.3 in diethyl ether; 1H NMR (CDCl3) δ8.35 (br m, NH), 7.56 (d, J=1.5 Hz, 1H), 7.29 (dd, J=1.7 and 8.6 Hz, 1H0, 7.22 (d, J=8.7 Hz, 1H), 7.08 (br s, 1H), 4.26 (dd, J=5.1 and 9.4 Hz, 1H), 3.28 (dd, J=9.4 and 18.3 Hz, 1H), 3.11 (s, 3H), 2.87 (dd, J=5.1 and 18.3 Hz, 1H); FAB LRMS (m/z, relative intensity, NH4 +as ionization source) 326 ([M(with 81Br)NH4 ]+, 100), 324 ([M(with 79Br)NH4 ]+, 96), 309 ([M(with 81Br)H]=, 21), 307 ([M(with 79Br)H]+, 20). Anal. calcd for C13H11BrN2O2 : C, 50.84; H, 3.61; N, 9.12. Found: C, 50.67; H, 3.43; N, 9.00.

Workup

  1. temperatureat reflux under nitrogen for 120 hours
  2. customThe resulting reaction mixture
  3. customwas evaporated under reduced pressure
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-d5a33cbe51704fbc90f90c8d33ab30a8
Source dataset
uspto-grants-1999_08
Patent number
US05942524

Reaction notes

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