Potassium Carbonate → Methyl 1-(isoquinolin-1-yl)-1H-indole-3-carboxylate

HRID 492174Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:10].Cl[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][N:22]=1>CS(C)=O.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][N:22]=2)[CH:12]=1)=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

1.73 g (12.5 mmol) of potassium carbonate are added at 20° C. under an argon atmosphere to 0.876 g (5 mmol) of 3-methoxycarbonyl-1H-indole in 10 cm3 of dimethyl sulphoxide. After stirring at 20° C. for 1 hour, 0.818 g (5 mmol) of 1-chloroisoquinoline is added. After stirring at 100° C. for 19 hours, the reaction mixture is cooled and diluted with 20 cm3 of ethyl acetate and then washed with 3 times 20 cm3 of water and 20 cm3 of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.35 g of 3-methoxycarbonyl-1-(isoquinol-1-yl)-1H-indole in the form of a white solid melting at 140° C.

Workup

stirringAfter stirring at 100° C. for 19 hours
temperaturethe reaction mixture is cooled
washwashed with 3 times 20 cm3 of water and 20 cm3 of saturated aqueous sodium chloride solution
customAfter separating the phases
dry with materialthe organic phase is dried over anhydrous magnesium sulphate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record: ord-9d0597202c1f45db82d220bef0a2ac24
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531663B2

Reaction notes

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