Tetrabutylammonium Fluoride → [3-(3-Methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanol

HRID 2196454Notes

Reaction equation

HRID 2196454 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:29]=[C:30]([C:34]2[CH:35]=[CH:36][C:37]3[N:38]([C:40]([CH3:48])=[C:41]([C:43]4[S:44][CH:45]=[CH:46][CH:47]=4)[N:42]=3)[CH:39]=2)[CH:31]=[CH:32][CH:33]=1)(C(C)(C)C)(C)C>O1CCCC1>[CH3:48][C:40]1[N:38]2[CH:39]=[C:34]([C:30]3[CH:29]=[C:28]([CH2:27][OH:26])[CH:33]=[CH:32][CH:31]=3)[CH:35]=[CH:36][C:37]2=[N:42][C:41]=1[C:43]1[S:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68638439HCID 68638439, compound

Product 1

HCID 44231018[3-(3-Methyl-2-thien-2-ylimidazo[1,2-a]pyridin-6-yl)phenyl]methanolYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

310 mg of tetrabutylammonium fluoride are introduced into a round-bottomed flask containing 260 mg of 6-[3-(tert-butyldimethylsilanyloxymethyl)phenyl]-3-methyl-2-thien-2-ylimidazo[1,2-a]pyridine in 6 ml of tetrahydrofuran. The reaction mixture is stirred at ambient temperature for 48 h and is concentrated under reduced pressure. The residue is purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 140 mg of compound are obtained. M+H=321

Workup

  1. concentrationis concentrated under reduced pressure
  2. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-ee5ffb87014d4434b584312c6e516c9a
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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