Tetrabutylammonium Fluoride → HCID 67170071, compound

HRID 877350Notes

Reaction equation

HRID 877350 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[N:17]=[N:18][N:19]([CH2:21][Si](C)(C)C)[CH:20]=2)[NH:9][S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[N:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[NH:9][S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67169978HCID 67169978, compound

Product 1

HCID 67170071HCID 67170071, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g (2.3 mmol) N-((S)-(4-bromophenyl){1-[(trimethylsilyl)-methyl]-1H-1,2,3-triazol-4-yl}methyl)-2-methylpropane-2-sulfinamide in 5.0 ml THF was added 2.5 mL (2.5 mmol) 1.0M solution TBAF. After 30 min at room temperature, the reaction mixture was concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-10% MeOH:Methylene chloride) afforded 0.80 g (95%) N-[(S)-(4-bromophenyl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-methylpropane-2-sulfinamide. 1H NMR (CDCl3, 400 MHz) 7.51-7.49 (m, 2H); 7.31 (m, 2H); 7.21 (s, 1H); 5.70 (d, 1H, J=2.96 Hz); 4.49 (d, 1H, J=2.75 Hz); 4.04 (s, 3H); 1.24 (s, 9H). ESMS [M+1]+=373.0.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customPurification by flash chromatography (silica gel, linear gradient 0-10% MeOH:Methylene chloride)

Sources & evidence

ORD record
ord-a124d643387b4d04a72e2780f338af5c
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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