Tetrabutylammonium Fluoride → HCID 9819174, compound

HRID 1245006Notes

Reaction equation

HRID 1245006 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]([Si](C(C)C)(C(C)C)C(C)C)[CH:28]=[C:29]([C:37]3([OH:43])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)[C:30]=2[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)=[CH:22][CH:21]=1>O1CCCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[NH:27][CH:28]=[C:29]([C:37]3([OH:43])[CH2:38][CH2:39][NH:40][CH2:41][CH2:42]3)[C:30]=2[C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21922760HCID 21922760, compound

Product 1

HCID 9819174HCID 9819174, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.73 ml (2.73 mmol) of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran were added to a solution of 675 mg (1.37 mmol) of 2-(4-fluorophenyl)-4-(4-hydroxypiperidin-4-yl)-3-(pyridin-4-yl)-1-triisopropylsilyl-1H-pyrrole [prepared as described in Example 9(iii) above] in 14 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 30 minutes. At the end of this time, the solvent was distilled off under reduced pressure. Water was added to the resulting residue and the precipitate thus obtained was collected by filtration and then washed with ethyl acetate to give 363 mg (yield 79%) of the title compound as a white powder.

Workup

  1. distillationAt the end of this time, the solvent was distilled off under reduced pressure
  2. additionWater was added to the resulting residue
  3. customthe precipitate thus obtained
  4. filtrationwas collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-8a3e176e32a54291afa51b858ee1bda9
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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