Tetrabutylammonium Fluoride → HCID 10359151, compound

HRID 1271863Notes

Reaction equation

HRID 1271863 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][O:29][Si](C(C)(C)C)(C)C)=[CH:25][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:27][CH2:28][OH:29])=[CH:25][C:19]=2[CH:18]=1)=[O:16]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69489781HCID 69489781, compound

Product 1

HCID 10359151HCID 10359151, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 55 mg (0.100 mmol) [2-({5-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-benzo[b]thiophene-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester (40) in 5 ml tetrahydrofurane was added 38 mg (0.120 mmol) tetra-n-butylammonium fluoride. The reaction mixture was stirred at room temperature for 1 h and poured into brine. The aqueous phase was extracted with ethyl acetate and the combined organic phases were washed brine and dried over sodium sulfate. The solvent was evaporated and the residue of (2-{[5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester was dissolved in 1.0 ml trifluoroacetic acid. The reaction mixture was stirred for 45 min at room temperature and then added to an aqueous solution of sodium bicarbonate. After extraction with ethyl acetate and removal of the solvent the residue was recrystallized from ethyl acetate/diethyl ether to yield 17 mg (0.052 mmol) of 5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carboxylic acid (2-amino-phenyl)-amide (39) as a white solid, mp. 215–216° C.

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate
  2. washthe combined organic phases were washed brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. dissolutionthe residue of (2-{[5-(2-Hydroxy-ethoxy)-benzo[b]thiophene-2-carbonyl]-amino}-phenyl)-carbamic acid tert-butyl ester was dissolved in 1.0 ml trifluoroacetic acid
  6. stirringThe reaction mixture was stirred for 45 min at room temperature
  7. additionadded to an aqueous solution of sodium bicarbonate
  8. extractionAfter extraction
  9. customwith ethyl acetate and removal of the solvent the residue
  10. customwas recrystallized from ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-d9dde0876ffc47398e9fc6472d29a1eb
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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