N-Ethyl-1-naphthalenamine → Ethyl 7-bromo-3-(3-(ethyl(naphthalen-1-yl)amino)propyl)-1h-indole-2-carboxylate

HRID 2095278Notes

Reaction equation

HRID 2095278 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.[CH2:20]([NH:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.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:22]([CH2:20][CH3:21])[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 67043N-Ethyl-1-naphthalenamineHCID 5049666Sodium triacetoxyborohydrideHCID 86628021ethyl 7-bromo-3-(3-oxopropyl)-1H-indole-2-carboxylate

Product 1

HCID 68938635Ethyl 7-bromo-3-(3-(ethyl(naphthalen-1-yl)amino)propyl)-1h-indole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 531A (130 mg) and N-ethylnaphthalen-1-amine (82 mg) in dichloromethane (3 mL) was added sodium triacetoxyborohydride (2.35 g). The mixture was stirred at room temperature overnight. After this time the mixture was diluted with ethyl acetate (1500 mL) and washed with 1N NaOH, water, brine, and dried over Na2SO4. After filtration and concentration of the filtrate, the residue was purified by flash chromatography using silica gel and eluenting with 5% ethyl acetate in hexane.

Workup

  1. washwashed with 1N NaOH, water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration of the filtrate
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-faf38a4fa13644878ffffece46e4158a
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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