Tetrabutylammonium Fluoride → HCID 9945215, compound

HRID 353087Notes

Reaction equation

HRID 353087 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[C:15]([CH2:16][CH3:17])=[C:14]([S:18][C:19]2[CH:20]=[C:21]([C:27]#[N:28])[CH:22]=[C:23]([CH:26]=2)[C:24]#[N:25])[C:13]([CH2:29][CH3:30])=[N:12]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[CH2:29]([C:13]1[C:14]([S:18][C:19]2[CH:26]=[C:23]([C:24]#[N:25])[CH:22]=[C:21]([CH:20]=2)[C:27]#[N:28])=[C:15]([CH2:16][CH3:17])[N:11]([CH2:10][CH2:9][OH:8])[N:12]=1)[CH3:30]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69554520HCID 69554520, compound

Product 1

HCID 9945215HCID 9945215, compoundYield 53.6%

Procedure

5-{[1-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-3,5-diethyl-1H-pyrazol-4-yl]sulfanyl}isophthalonitrile (180 mg, 0.4 mmol) (Preparation 51) was treated with tetrabutylammonium fluoride (1M solution in tetrahydrofuran, 0.8 ml, 0.8 mmol) and the resulting solution was stirred for 2½ hours. The mixture was concentrated under reduced pressure to give a brown oil. The crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:4, by volume) to provide the title compound (70 mg) as a yellow oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a brown oil
  3. customThe crude product was purified by flash chromatography on silica gel eluting with ethyl acetate:dichloromethane (1:4, by volume)

Sources & evidence

ORD record
ord-d1f978fddeb340a09238f0f3210bffe8
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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