Carbon Tetrachloride → 3-Chloro-5-(4-isopropoxyphenyl)-1-(6-isopropoxypyrid-3-yl)indole-2-carboxylic acid ethyl ester

HRID 646133Notes

Reaction equation

ClN1C(=O)C[CH2:4][C:3]1=O.[CH:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[N:24]([C:28]2[CH:29]=[N:30][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:32][CH:33]=2)[C:23]([C:38]([OH:40])=[O:39])=[CH:22]3)=[CH:15][CH:14]=1)([CH3:11])[CH3:10].C(Cl)(Cl)(Cl)[Cl:42]>CCOC(C)=O>[CH2:3]([O:39][C:38]([C:23]1[N:24]([C:28]2[CH:29]=[N:30][C:31]([O:34][CH:35]([CH3:36])[CH3:37])=[CH:32][CH:33]=2)[C:25]2[C:21]([C:22]=1[Cl:42])=[CH:20][C:19]([C:16]1[CH:15]=[CH:14][C:13]([O:12][CH:9]([CH3:10])[CH3:11])=[CH:18][CH:17]=1)=[CH:27][CH:26]=2)=[O:40])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

N-Chlorosuccinimide (37 mg, 280 nmol) and 5-(4-isopropoxyphenyl)-1-(6-isopropoxypyrid-3-yl)indole-2-carboxylic acid ethyl ester (117 mg, 255 nmol; see Example 17) were mixed in CCl4 (2 mL) and stirred at 80° C. for 2 h. The mixture was diluted with EtOAc and washed with Na2S2O3 (aq., 10%) and NaHCO3 (aq., sat.). The combined extracts were washed with water, brine and dried over Na2SO4. Concentration gave the sub-title compound (116 mg, 92%).

Workup

washwashed with Na2S2O3 (aq., 10%) and NaHCO3 (aq., sat.)
washThe combined extracts were washed with water, brine
dry with materialdried over Na2SO4
concentrationConcentration

Sources & evidence

ORD record: ord-ab4b4ae233bf4bf68eee178cee2d0d75
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705023B2

Reaction notes

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