Tetrabutylammonium Fluoride → HCID 86614281, compound

HRID 923211Notes

Reaction equation

HRID 923211 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]3[N:14]([C:18]([C:21]#[C:22][Si](C)(C)C)=[CH:19][N:20]=3)[CH:15]=[CH:16][CH:17]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CO.C(Cl)Cl>C1COCC1>[C:21]([C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:13]2=[N:20][CH:19]=1)#[CH:22]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 21226129Dichloromethane methanolHCID 66735589HCID 66735589, compound

Product 1

HCID 86614281HCID 86614281, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-(methylsulfonyl)phenyl)-3-((trimethylsilyl)ethynyl)imidazo[1,2-a]pyridin-8-amine (0.058 g, 0.15 mmol) in 1.5 mL of THF was added 0.23 mL (0.23 mmol) of tetrabutylammonium fluoride (1.0M in THF) at ambient temperature. The solution was stirred for 15 min, concentrated, and the crude product purified by silica gel flash chromatography (triethylamine-treated silica gel; eluted with 100% DCM then 5% MeOH/DCM) to provide a quantitative yield (0.047 g) of product: 312 m/z (M+H).

Workup

  1. concentrationconcentrated
  2. customthe crude product purified by silica gel flash chromatography (triethylamine-
  3. additiontreated silica gel
  4. washeluted with 100% DCM

Sources & evidence

ORD record
ord-321c68ec13f9443cbef121ba901b2f8e
Source dataset
uspto-grants-2016_03
Patent number
US09278971B2

Reaction notes

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