Potassium Carbonate → 3-ethoxycarbonyl-4-trifluoromethyl-1-(isoquinolin-1-yl)-1H-pyrrole

HRID 1792824Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

1.04 g (5 mmol) of 3-ethoxycarbonyl-4-trifluoromethyl-1H-pyrrole and 0.818 g (5 mmol) of 1-chloroisoquinoline are added to 1.73 g (12.5 mmol) of potassium carbonate suspended in 10 mL of dimethyl sulphoxide at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 17 hours at a temperature in the region of 110° C., the reaction mixture is cooled and then diluted with 30 mL of water. The solid formed is filtered off and washed with water and then oven-dried under reduced pressure (2.7 kPa), giving 1.46 g of 3-ethoxycarbonyl-4-trifluoromethyl-1-(isoquinolin-1-yl)-1H-pyrrole in the form of cream-colored crystals. IR spectrum (KBr), 3159; 2983; 2937; 1721; 1628; 1555; 1534; 1502; 1405; 1343; 1290; 1272; 1215; 1179; 1151; 1135; 1120; 1035; 831; 809; 755; 679 and 674 cm−1. Mass spectrum (EI) m/e 334 (M+.), m/e 289.

Workup

temperaturethe reaction mixture is cooled
customThe solid formed
filtrationis filtered off
washwashed with water
customoven-dried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-f8b8ad23069441068da762ab746c7678
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07078414B2

Reaction notes

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