Dimethyl Sulfide → HCID 51347785, compound

HRID 2370989Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[N:8]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:30])[O:4][N:3]=1.B(F)(F)F.S(C)C>C(Cl)Cl.CO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([S:24]([N:27]([CH3:28])[CH3:29])(=[O:26])=[O:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:30])[O:4][N:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(3,5-dimethylisoxazol-4-yl)-3-(4-methoxyphenyl)-N,N-dimethyl-1H-indole-1-sulfonamide (23 mg, 0.05 mmol) was dissolved in DCM and the mixture was cooled at 0° C. BF3.SMe2 (0.7 ml) was added drop wise and the reaction mixture was stirred in the fridge for 16 h. A few drops MeOH were added to the cool mixture. The mixture was then extracted with H2O/DCM using an isolute phase separator. Concentration gave a crude product which was purified using HPLC (40-70% AcN, 25 min gradient). 5.6 mg 2-(3,5-dimethylisoxazol-4-yl)-3-(4-hydroxyphenyl)-N,N-dimethyl-1H-indole-1-sulfonamide was obtained. ES/MS m/z: 412.06 (M+H), 410.16 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.18 (m, 1H), 7.60 (m, 1H), 7.43 (m, 1H), 7.34 (m, 1H), 7.12 (m, 2H), 6.88 (m, 2H), 2.70 (s, 6H), 2.10 (s, 3H) and 2.09 (s, 3H).

Workup

extractionThe mixture was then extracted with H2O/DCM using an isolute phase separator
concentrationConcentration
customgave a crude product which
customwas purified
customHPLC (40-70% AcN, 25 min gradient)

Sources & evidence

ORD record: ord-cb4b8f66435244d881dd0ab4a3c169a1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710243B2

Reaction notes

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