Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate → 4-(Trifluoromethyl)-7-(benzyloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 565003Notes

Reaction equation

HRID 565003 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:27]([O-])=O)=[C:11]([CH2:19][C:20](=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cl-].[Ti+4].[Cl-].[Cl-].[Cl-].C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[C:11]2[C:10]=1[NH:27][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54393638Ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate

Product 1

HCID 211940524-(Trifluoromethyl)-7-(benzyloxy)-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 160960Diamminetetrachlorotitanate(IV)CatalystHCID 702EthanolSolvent

Procedure

The reaction was carried out in a manner similar to Reference Example 12 c) except for using 10.9 g (26.7 mmol) of ethyl (3-benzyloxy-6-trifluoromethyl-2-nitrophenyl)pyruvate, 165 g (213 mol) of 20% titanium chloride aqueous solution and 100 ml of ethanol. Ethyl 7-benzyloxy-4-trifluoromethyl-2-indolecarboxylate was thus obtained in the yield of 8.00 g (82.6%).

Sources & evidence

ORD record
ord-0fa28aba0f1c4478b2c8abca45343c25
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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