Tetrabutylammonium Fluoride → N-(4-(benzyloxy)pyridin-3-yl)methanesulfonamide

HRID 44111Notes

Reaction equation

[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[N:33](S(C)(=O)=O)[S:34]([CH3:37])(=[O:36])=[O:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Tetrabutylammonium fluoride 1M in THF (12.2 ml, 42 mmol, 2.5 eq) was added to a solution of N-(4-(benzyloxy)pyridin-3-yl)-N-(methylsulfonyl)methane sulfonamide (6 g, 16.8 mmol, 1 eq) in THF at room temperature. The reaction mixture was refluxed at 60° C. for 10 h. The solution was concentrated completely and diluted with water (5 mL) and was allowed to stir for 15 minutes. The solid precipitated was filtered, washed with water and dried under vacuum yielding the expected product as a pale brown solid. 1HNMR (400 MHz, DMSO-d6): δ 3.35 (s, 3H), 5.27 (s, 2H), 7.21 (d, J=5.64 Hz, 1H), 7.36-7.54 (m, 3H), 7.54 d, J=7.28 Hz, 2H), 8.30 (s, 1H), 8.33 (d, J=5.64 Hz, 1H), 9.34 (s, 1H).

Workup

concentrationThe solution was concentrated completely
additiondiluted with water (5 mL)
customThe solid precipitated
filtrationwas filtered
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-7361d88502204438bf31864992b840b5
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536338B2

Reaction notes

Loading…