Indole → HCID 69209823, compound

HRID 2054135Notes

Reaction equation

HRID 2054135 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=NN=1)=[O:5])[CH3:2].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1>C(Cl)Cl>[C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=[N:8][C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:18]2[C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=1[NH:17]2

Participants

4

Reactant 2

HCID 798IndoleHCID 14200494HCID 14200494, compound

Product 1

HCID 69209823HCID 69209823, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5.71 (318 mg, 1.61 mmol) in anhydrous methylene chloride (15 mL) was added a solution of indole (100 mg, 0.85 mmol) in anhydrous methylene chloride (50 mL) dropwise over 4 h with stirring at mild reflux. Following the addition, stirring was continued for 4 h and the reaction mixture was then cooled down. After filtration, the filtrate was evaporated under (reduced pressure and the residue oil was submitted to chromatography (flash column, silica gel, methylene chloride:ethyl acetate=1:1, v/v as eluent) to afford the title compound 5.72 as an orange solid (132 mg, 52%), mp. 151-152° C. 1H NMR (200 MHz, CDCl3) δ (ppm): 11.10 (s, 1H), 8-63 (d, J=8.2 Hz, 1H), 7.63 (d, J=7.6 Hz, 1H), 7.50 (t, J=7.0 Hz, 1H), 7.26 (t, J=7.0 Hz, 1H), 4.62 (q, J=7.0 Hz, 2H), 4.47 (q, J=7-0 Hz, 2H), 1.44 (I:, J=7.0 Hz, 3H), 1.34 (t, J=7.0 Hz, 3H). Anal. (C16H15N3O4) C, H, N.

Workup

  1. additionthe addition
  2. stirringstirring
  3. temperaturethe reaction mixture was then cooled down
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated under (reduced pressure

Sources & evidence

ORD record
ord-03c8dfc4007840ca83830b5c0b235678
Source dataset
uspto-grants-2008_02
Patent number
US07329651B2

Reaction notes

Loading…