Carbon Tetrachloride → 3-chloro-5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acid ethyl ester

HRID 646142Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][N:16]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2].C(Cl)(Cl)(Cl)[Cl:26]>CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[Cl:26])=[CH:12][C:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:23])([F:24])[F:22])=[CH:17][N:16]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

N-Chlorosuccimimide (480 mg, 3.86 mmol) and 5-(5-trifluoromethylpyrid-2-yl)-1H-indole-2-carboxylic acid ethyl ester (800 mg, 2.4 mmol; see Example 8 (b)) were mixed in CCl4 (50 mL) and stirred at 80° C. for 2 h. The mixture was diluted with EtOAc and washed with Na2S2O3 (aq., sat.), NaHCO3 (aq., sat.), brine and dried over Na2SO4 Concentration gave the sub-title compound (870 mg, 98%).

Workup

washwashed with Na2S2O3 (aq., sat.), NaHCO3 (aq., sat.), brine
dry with materialdried over Na2SO4 Concentration

Sources & evidence

ORD record: ord-c5099cb5a3a548c588d7aee20c6ccf6a
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705023B2

Reaction notes

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