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

HRID 219420Notes

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 1 M 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 335 (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-db637160f1bd43a2ae89842994cfe219
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198449B2

Reaction notes

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