Ethylamine → 1-ethylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

HRID 19563Notes

Reaction equation

HRID 19563 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7](Br)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].[CH2:24]([NH2:26])[CH3:25]>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([NH:26][CH2:24][CH3:25])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 686984701-bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

Product 1

HCID 116957491-ethylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl esterYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Bromo-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (100 mg, 0.27 mmol) obtained in Example 18 was dissolved in THF (10 mL), and 2.0 M ethylamine (0.68 mL, 1.35 mmol) in THF was added dropwise thereto. The mixture was stirred for 12 hrs at RT, and the solvent was removed under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 68 mg of the titled compound (yield: 75.6%).

Workup

  1. customthe solvent was removed under a reduced pressure
  2. customThe resulting residue was purified by flash chromatography

Sources & evidence

ORD record
ord-8ecd8a7401944feb92db26b3c667f74b
Source dataset
uspto-grants-2010_06
Patent number
US07745439B2

Reaction notes

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