4-(1H-Indol-6-yl)morpholine → Benzyl 2-methyl-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

HRID 2361291Notes

Reaction equation

HRID 2361291 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[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][C:7]([N:10]4[CH2:15][CH2:14][O:13][CH2:12][CH2:11]4)=[CH:6][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 219558904-(1H-Indol-6-yl)morpholineHCID 67995173(E)-Benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate

Product 1

HCID 67994689Benzyl 2-methyl-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenylcarbamateYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(1H-indol-6-yl)morpholine (1.1132 g, 5.50 mmol) and (E)-benzyl 2-methyl-3-(2-nitrovinyl)phenylcarbamate (2.58 g, 8.26 mmol) in THF (50 mL) was concentrated in vacuo. The residue was melted at 137° C. and stirred overnight. After cooling to room temperature, the crude product was purified by flash chromatography using an ISCO 330 g column (solid loading) eluting with 40-80% EtOAc/hexanes to give the desired product (0.9544 g, 1.855 mmol, 33.7% yield) as a light brown solid.

Workup

  1. customthe crude product was purified by flash chromatography
  2. washeluting with 40-80% EtOAc/hexanes

Sources & evidence

ORD record
ord-7fb47ee57e6546fcbe9b6534d14466e8
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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