4-(1H-Indol-5-yl)morpholine → Benzyl 2-methyl-3-(1-(5-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

HRID 2361343Notes

Reaction equation

HRID 2361343 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:16][C:17]1[C:22](/[CH:23]=[CH:24]/[N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C1COCC1>[CH3:16][C:17]1[C:22]([CH:23]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[C:6]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)[CH:5]=3)[NH:1][CH:2]=2)[CH2:24][N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=[CH:19][C:18]=1[NH:28][C:29](=[O:38])[O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 114014384-(1H-Indol-5-yl)morpholineHCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

Product 1

HCID 67994839Benzyl 2-methyl-3-(1-(5-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamateYield 37.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1H-Indol-5-yl)morpholine (1.102 g, 5.45 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (1.2154 g, 3.89 mmol) were dissolved in THF and concentrated in vacuo to dryness. The mixture was then melted at 140° C. After 5 h, the reaction was cooled to room temperature and purified by flash chromatography using an ISCO 120 g column eluting with 0-60% EtOAc/hexanes to give the desired product (0.8047 g, 1.454 mmol, 37.4% yield) as a tan foam.

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. custompurified by flash chromatography
  3. washeluting with 0-60% EtOAc/hexanes

Sources & evidence

ORD record
ord-48452d3f8f1b4469b2370eedf60da771
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…