Water → 3-ethoxycarbonyl-4-trifluoromethyl-1-(quinolin-4-yl)-1H-pyrrole

HRID 1792822Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10]([C:12]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][NH:14][CH:13]=1)=[O:11])[CH3:8].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.O>CS(C)=O>[CH2:7]([O:9][C:10]([C:12]1[C:16]([C:17]([F:20])([F:18])[F:19])=[CH:15][N:14]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH:13]=1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 110 °C

Procedure

1.73 g (12.5 mmol) of potassium carbonate are added to 1.036 g (5 mmol) of 3-ethoxycarbonyl-4-trifluoromethyl-1H-pyrrole and 0.82 g (5 mmol) of 4-chloroquinoline dissolved in 10 mL of dimethyl sulphoxide at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 18 hours at a temperature in the region of 110° C., the reaction mixture is poured into 30 mL of water and then left to crystallize for 1 hour at 20° C. After the solid residue has been filtered off and air-dried, 1.48 g of 3-ethoxycarbonyl-4-trifluoromethyl-1-(quinolin-4-yl)-1H-pyrrole are obtained in the form of beige-colored crystals melting at 108° C. IR spectrum (KBr): 3139; 1718; 1564; 1537; 1511; 1306; 1281; 1249; 1169; 1146; 1123; 1036; 846 and 773 cm1.

Workup

waitleft
customto crystallize for 1 hour at 20° C
filtrationAfter the solid residue has been filtered off
customair-dried

Sources & evidence

ORD record: ord-3b5bd54644864a379c57521b24b68dd2
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078414B2

Reaction notes

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