N,N'-Dimethylethylenediamine → 1-Isopropyl-6-(methylsulfonyl)-1H-indole-4-carboxylic acid

HRID 42516Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[CH:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[CH3:18][S:19]([O-:21])=[O:20].[Na+].CNCCNC>CS(C)=O>[CH:11]([N:8]1[C:9]2[CH:10]=[C:2]([S:19]([CH3:18])(=[O:21])=[O:20])[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]=2[CH:6]=[CH:7]1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 165 °C

Procedure

To a 10-mL microwave tube were added methyl 6-bromo-1-(1-methylethyl)-1H-indole-4-carboxylate (160 mg, 0.540 mmol), sodium methanesulfinate (80 mg, 0.702 mmol), DMSO (2 mL), and N,N′-dimethyl-1,2-ethanediamine (6.19 mg, 0.070 mmol), and the mixture was degassed for 5 min by bubbling N2. Copper(I) trifluoromethanesulfonate benzene complex (25.6 mg, 0.043 mmol) was added and the mixture was heated to 165° C. for 2 h with stirring. The mixture was filtered and the DMSO solution was purified using reverse-phase HPLC to give 14 mg of product as white solid. 1H NMR (400 MHz, DMSO-d6) ppm 1.51 (d, J=4.00 Hz, 6H), 4.90-5.11 (m, 1H), 7.13 (d, J=3.03 Hz, 1H), 7.98-8.08 (m, 1H), 8.15-8.23 (m, 1H), 8.32-8.46 (m, 1H), 13.19 (br. s., 1H). MS: (M+H)+=281.9.

Workup

customthe mixture was degassed for 5 min
customby bubbling N2
additionCopper(I) trifluoromethanesulfonate benzene complex (25.6 mg, 0.043 mmol) was added
filtrationThe mixture was filtered
customthe DMSO solution was purified

Sources & evidence

ORD record: ord-3cec4fd0a5274151a8e24be020b9b9fa
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536179B2

Reaction notes

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