1,2,3,4-Tetrahydroquinoline → Ethyl 7-bromo-3-(3-(3,4-dihydroquinolin-1(2h)-yl)propyl)-1h-indole-2-carboxylate

HRID 2199724Notes

Reaction equation

HRID 2199724 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH:18]=O.[NH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:21]1.C([O-])(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 517045Sodium AcetateHCID 86628021ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

Product 1

HCID 68937693Ethyl 7-bromo-3-(3-(3,4-dihydroquinolin-1(2h)-yl)propyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of EXAMPLE 103A (325 mg) and 1,2,3,4-tetrahydroquinoline (160 mg) in dichloroethane (10 mL) was added sodium acetate (310 mg). The mixture was stirred at ambient temperature overnight, diluted with ethyl acetate (200 mL) and washed with 1N NaOH, water, and brine. After drying over sodium sulfate and concentration, the concentrate was loaded on a silica gel cartridge and eluted with 5% ethyl acetate in hexane.

Workup

  1. washwashed with 1N NaOH, water, and brine
  2. dry with materialAfter drying over sodium sulfate and concentration
  3. washeluted with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-689e4d24cb444e948bca2b5a5f07f766
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

Loading…