2-(benzyloxy)-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide → 2-hydroxy-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide

HRID 1630960Notes

Reaction equation

C([O:8][CH2:9][CH2:10][S:11]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=1)(=[O:13])=[O:12])C1C=CC=CC=1>[Pd].CO>[OH:8][CH2:9][CH2:10][S:11]([NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[N:22]([CH3:30])[C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:20]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

A flask is charged with 2-(benzyloxy)-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide (90 mg, 0.214 mmol) and MeOH (5 mL), and the flask is flushed with N2. 10% Pd/C (22.7 mg, 0.021 mmol) is added to the mixture. The flask is flushed with H2 and stirred under H2 atmosphere at 50° C. overnight. The mixture is filtered and the filtrate is purified by silica chromatography eluting with a 0 to 4% methanol-DCM gradient to give 2-hydroxy-N-(5-(1-methyl-1H-indol-2-yl)pyridin-3-yl)ethanesulfonamide. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.37 (t, J=6.2 Hz, 2H), 3.77 (s, 3H), 3.80 (t, J=6.3 Hz, 2H), 4.96 (br. s., 1H), 6.70 (s, 1H), 7.10 (t, J=7.1 Hz, 1H), 7.23 (td, J=7.6, 1.1 Hz, 1H), 7.53 (d, J=7.8 Hz, 1H), 7.61 (d, J=7.8 Hz, 1H), 7.79 (t, J=2.3 Hz, 1H), 8.47 (d, J=2.5 Hz, 1H), 8.55 (d, J=1.8 Hz, 1H), 10.12 (br. s., 1H). HRMS: (ESI) m/z 332.1072 [(M+H)+ Calcd for C16H18N3O3S 332.1063].

Workup

customthe flask is flushed with N2
customThe flask is flushed with H2
filtrationThe mixture is filtered
customthe filtrate is purified by silica chromatography
washeluting with a 0 to 4% methanol-DCM gradient

Sources & evidence

ORD record: ord-b3837fed269545b7b5a43a3e3e2b5cfc
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791141B2

Reaction notes

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