Tetrabutylammonium Fluoride → HCID 131723205, compound

HRID 843664Notes

Reaction equation

HRID 843664 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([N:11]([CH2:34][CH2:35][CH3:36])[CH2:12][C:13]1[N:17]([CH2:18][CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][C:23]([CH2:25][O:26][Si](C)(C)C(C)(C)C)=[CH:24][C:15]=2[N:14]=1)=[O:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([N:11]([CH2:12][C:13]1[N:17]([CH2:18][CH2:19][CH3:20])[C:16]2[CH:21]=[CH:22][C:23]([CH2:25][OH:26])=[CH:24][C:15]=2[N:14]=1)[CH2:34][CH2:35][CH3:36])=[O:10]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69314684HCID 69314684, compound

Product 1

HCID 131723205HCID 131723205, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution 1.25 g (2.4 mmole) of (2,5-difluorophenyl)-N-propyl-N-({1-propyl-5-[(1,1,2,2-tetramethyl-1-silapropoxy)methyl]benzimidazol-2-yl}methyl)carboxamide in 20 mL of THF is treated at room temperature with 3 mL of 1M tetrabutylammonium fluoride for 1 hr. The reaction solution is diluted with 20 mL of sat NaHCO3 and extracted with 3×100 mL of dichloromethane. The organic extracts are dried over anhydrous Na2SO4 and the solvent removed in vacuo to afford 0.96 g (99%) of (2,5-difluorophenyl)-N-{[5-(hydroxymethyl)-1-propylbenzimidazol-2-yl]methyl}-N-propylcarboxamide.

Workup

  1. extractionextracted with 3×100 mL of dichloromethane
  2. dry with materialThe organic extracts are dried over anhydrous Na2SO4
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-243c093a51c447c38af11938c0d6433f
Source dataset
uspto-grants-2002_04
Patent number
US06380210B1

Reaction notes

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