5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-7-(trifluoromethyl)-9H-pyrido[2,3-b]indole acetate → 5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-9H-pyrido[2,3-b]indole-7-carboxylic acid

HRID 1642535Notes

Reaction equation

[C:1]([OH:4])(=[O:3])[CH3:2].[CH2:5]([S:7]([C:10]1[CH:11]=[C:12]([C:16]2[CH:24]=[C:23](C(F)(F)F)[C:22](C)=[C:21]3[C:17]=2[C:18]2[CH:33]=[C:32]([CH3:34])[CH:31]=[N:30][C:19]=2[NH:20]3)[CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8])[CH3:6]>OS(O)(=O)=O>[CH2:5]([S:7]([C:10]1[CH:11]=[C:12]([C:16]2[CH:24]=[C:2]([C:1]([OH:4])=[O:3])[C:22]([CH3:23])=[C:21]3[C:17]=2[C:18]2[CH:33]=[C:32]([CH3:34])[CH:31]=[N:30][C:19]=2[NH:20]3)[CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8])[CH3:6]

Participants

Conditions

Temperature: 120 °C

Procedure

5-(3-(ethylsulfonyl)phenyl)-3,8-dimethyl-7-(trifluoromethyl)-9H-pyrido[2,3-b]indole acetate (3.6 g, 7.3 mmol) was dissolved in concentrated H2SO4 (30 mL) and heated at 120° C. for 30 min. The reaction was cooled to room temperature and poured over ice affording a white precipitate. The resulting suspension was filtered, rinsed with H2O (3×30 mL) followed by IPA (3×10 mL) and dried in vacuo to 3.2 g (quant.) to give the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.20 (s, 1H), 8.36 (s, 1H), 8.12 (s, 1H), 8.02-8.07 (m, 2H), 7.89 (t, 1H), 7.61 (s, 1H), 7.54 (s, 1H), 3.43 (q, 2H), 2.85 (s, 3H), 2.28 (s, 3H), 1.18 (t, 3H). MS (ES) [m+H] calc'd for C22H20N2O4S, 409; found 409.3.

Workup

temperatureThe reaction was cooled to room temperature
additionpoured over ice affording a white precipitate
filtrationThe resulting suspension was filtered
washrinsed with H2O (3×30 mL)
customdried in vacuo to 3.2 g (quant.)

Sources & evidence

ORD record: ord-9df4cc4603d147b39395ed61b44b86c6
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119655B2

Reaction notes

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