Hexane → HCID 68544686, compound

HRID 2245504Notes

Reaction equation

HRID 2245504 reaction equation
[C:1]([C:5]1[CH:30]=[CH:29][C:8]([CH2:9][N:10]2[C:18]3[C:13](=[CH:14][C:15]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:22])=[O:21])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:33][O:34][C:35](=[O:38])[CH2:36]Br.CCCCCC>CN(C=O)C.CCOC(C)=O>[CH3:33][O:34][C:35](=[O:38])[CH2:36][N:19]([S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:22])[C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([CH2:9][C:8]1[CH:29]=[CH:30][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=1)[CH:11]=[CH:12]2

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 68545398HCID 68545398, compound

Product 1

HCID 68544686HCID 68544686, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-[1-(4-tert-butyl-benzyl)-1H-indol-5-yl]-benzenesulfonamide (0.20 g, 0.48 mmol) in DMF (5 ml) at room temperature under a nitrogen atmosphere was added sodium hydride (60% dispersion in mineral oil, 0.03 g, 0.72 mmol) in one portion. The resulting brown mixture was stirred 10 minutes upon which bromo-acetic acid methyl ester was added (0.19 g, 0.96 mmol). After 90 minutes total reaction time, the reaction was quenched with water (2 ml). The brown solution was partitioned between EtOAc (15 ml) and H2O (10 ml) and the layers were separated. The aqueous layer was extracted with EtOAc (5 ml). All organics were combined, extracted with brine (3×10 ml), dried with MgSO4, filtered and concentrated in vacuo to afford a brown powder. Gradient SiO2 chromatography (Hexane:EtOAc) afforded {benzenesulfonyl-[1-(4-tert-butyl-benzyl)-1H-indol-5-yl]-amino}-acetic acid methyl ester as a pale red powder (0.18 g, 72% yield): MS (ESI) m/z 533.

Workup

  1. additionwas added (0.19 g, 0.96 mmol)
  2. customthe reaction was quenched with water (2 ml)
  3. customThe brown solution was partitioned between EtOAc (15 ml) and H2O (10 ml)
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted with EtOAc (5 ml)
  6. extractionextracted with brine (3×10 ml)
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto afford a brown powder

Sources & evidence

ORD record
ord-a97afa5786094d39b461236d1bb465f6
Source dataset
uspto-grants-2010_03
Patent number
US07683091B2

Reaction notes

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