Pyridine → 1-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester

HRID 420905Notes

Reaction equation

HRID 420905 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2].[F:33][C:34]([F:45])([F:44])[C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1.N1C=CC=CC=1.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Cu+2].C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][C:38]3[CH:39]=[CH:40][C:35]([C:34]([F:45])([F:44])[F:33])=[CH:36][CH:37]=3)[CH:13]=2)[N:8]([C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][CH:17]=2)[C:7]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 666576271-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester

Product 1

HCID 666576321-(4-Diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethylphenoxy)indole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-hydroxyindole-3-carboxylic acid ethyl ester (200 mg, 0.46 mmol, see step (b) above), Cu(OAc)2 (83 mg, 0.46 mmol), 4-trifluoromethylbenzeneboronic acid (129 mg, 0.68 mmol), pyridine (55 μL, 0.68 mmol), Et3N (94 μL, 0.68 mmol), molecular sieves 4 Å and anhydrous CH2Cl2 (10 mL) was stirred at rt for 2 d, filtered, concentrated and purified by chromatography to give the sub-title compound. Yield 150 mg, 56%.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. custompurified by chromatography

Sources & evidence

ORD record
ord-86aa35b4edab44f7adb188f9fdfdee87
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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