Tetrabutylammonium Fluoride → N-(1H-Indol-4-yl)-2-methylamino-N-phenyl-acetamide

HRID 268764Notes

Reaction equation

HRID 268764 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([N:6]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][N:11]2[Si](C(C)C)(C(C)C)C(C)C)=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH:11]1[C:12]2[C:8](=[C:7]([N:6]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:4](=[O:5])[CH2:3][NH:2][CH3:1])[CH:15]=[CH:14][CH:13]=2)[CH:9]=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 598318392-Methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide

Product 1

HCID 59831661N-(1H-Indol-4-yl)-2-methylamino-N-phenyl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of 2-methylamino-N-phenyl-N-(1-triisopropylsilanyl-1H-indol-4-yl)-acetamide XXIII in THF (5 ml) was added tetrabutylammonium fluoride (TBAF) (149 mg, 0.566 mmol). The mixture was stirred for 18 hours and then partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude N-(1H-indol-4-yl)-2-methylamino-N-phenyl-acetamide XXIV (122 mg, pale yellow solid) was used without further purification for the next reaction.

Workup

  1. custompartitioned between EtOAc
  2. extractionThe aqueous layer was extracted twice with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude N-(1H-indol-4-yl)-2-methylamino-N-phenyl-acetamide XXIV (122 mg, pale yellow solid) was used without further purification for the next reaction

Sources & evidence

ORD record
ord-d7da6e8551b34a93bb747a8fa1ecbccb
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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