2-Ethoxy-1-naphthoic acid → Ethyl [2-(2-ethoxy-naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate

HRID 2236110Notes

Reaction equation

HRID 2236110 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]([OH:16])=O)[CH3:2].CCN(C(C)C)C(C)C.Cl.[CH2:27]1[C:39]2[C:38]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:32]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:31]=2[CH2:30][CH2:29][NH:28]1>C1COCC1.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:14]([N:28]1[CH2:29][CH2:30][C:31]2[N:32]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][C:38]=3[C:39]=2[CH2:27]1)=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 752102-Ethoxy-1-naphthoic acidHCID 81531DiisopropylethylamineHCID 71552668Ethyl (1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate hydrochloride

Product 1

HCID 86614345Ethyl [2-(2-ethoxy-naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetateYield 94.2%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Step a): To a solution of 2-ethoxynaphthoic acid (22 mg, 0.1 mmol), N′,N′,N′,N′tetramethyl-O-(7-azabenzotriazole-1-yl)-uronium-hexafluorophosphate (38 mg, 0.1 mmol) and DIEA (51 μl, 0.3 mmol) in THF/DMF (4:1, 1 ml) is added Intermediate 1 (29 mg, 0.1 mmol) in one portion and the reaction mixture is stirred at rt overnight. Then, the solvent is evaporated and the residue purified by silica gel column chromatography (6% MeOH in CH2Cl2/aqueous NH4OH 9:1) affording ethyl [2-(2-ethoxy-naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate (43 mg) as a glassy brown solid in 93% yield.

Workup

  1. customThen, the solvent is evaporated
  2. customthe residue purified by silica gel column chromatography (6% MeOH in CH2Cl2/aqueous NH4OH 9:1)

Sources & evidence

ORD record
ord-1b0d2e6621bd4e08986703ae89efec85
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

Loading…