5-Bromoindole → HCID 15326267, compound

HRID 2289854Notes

Reaction equation

HRID 2289854 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-fc4215918d794975a7f720a33b8f27d7
Source dataset
uspto-grants-2000_07
Patent number
US06093822

Reaction notes

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