Sodium hydride → HCID 58975058, compound

HRID 737026Notes

Reaction equation

HRID 737026 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)[CH2:4][CH3:5].[F:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][NH:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[O:23])=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][NH:21][C:22](=[O:23])[C:24]2[CH:29]=[CH:28][C:27]([S:30]([N:8]3[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:6]([CH2:3][CH2:4][CH3:5])=[CH:7]3)(=[O:31])=[O:32])=[CH:26][CH:25]=2)=[CH:34][CH:35]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 12502665HCID 12502665, compoundHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 58975058HCID 58975058, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add NaH 60% in mineral oil (0.080 g, 2.0 mmol) to a stirred solution of 3-propyl-indole (0.266 g, 1.67 mmol) in dr THF (25 mL) under N2. Stir the reaction mixture at ambient temperature for 45 min. Add 4-(4-fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (0.547 g, 1.67 mmol) portion wise at ambient temperature. Stir the reaction mixture overnight at ambient temperature. Pour the reaction mixture into a two-phase mixture of EtOAc (150 mL) and saturated solution of NaHCO3 (50 mL). Separate the organic layer, wash with brine, separate and dry (MgSO4). Filter and evaporate the filtrate. Purify the residue on the chromatron using a 4 mm plate and eluting with a gradient hexane-EtOAC system to give 0.262 g (34%) of N-(4-fluoro-benzyl)-4-([3-propyl-indole-1-sulfonyl]-benzamide. Mass spectrum (m/e) M+1) 451.1.

Workup

  1. customwise at ambient temperature
  2. stirringStir the reaction mixture overnight at ambient temperature
  3. additionPour the reaction mixture
  4. customSeparate the organic layer
  5. washwash with brine
  6. customseparate
  7. dry with materialdry (MgSO4)
  8. filtrationFilter
  9. customevaporate the filtrate
  10. customPurify the residue on the chromatron
  11. washeluting with a gradient hexane-EtOAC system
  12. customto give 0.262 g (34%) of N-(4-fluoro-benzyl)-4-([3-propyl-indole-1-sulfonyl]-benzamide. Mass spectrum (m/e) M+1) 451.1

Sources & evidence

ORD record
ord-6c330a908e884327a0208dd42e5d46e1
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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