Sodium hydride → HCID 68278821, compound

HRID 1506924Notes

Reaction equation

HRID 1506924 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1[S:18][C:17]2[CH2:19][CH2:20][CH2:21][CH2:22][C:16]=2[C:15]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])(=[O:12])=[O:11].[CH3:28][Si:29]([CH3:36])([CH3:35])[CH2:30][CH2:31][O:32][CH2:33]Cl>C1COCC1>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([N:13]([C:14]1[S:18][C:17]2[CH2:19][CH2:20][CH2:21][CH2:22][C:16]=2[C:15]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:33][O:32][CH2:31][CH2:30][Si:29]([CH3:36])([CH3:35])[CH3:28])(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 68278840HCID 68278840, compound2×

Product 1

HCID 68278821HCID 68278821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% dispersion in oil, 0.081 g) was added to a solution of ethyl 2-(2-bromobenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Intermediate 39, 0.700 g) in anhydrous THF at 0° C. under nitrogen. The mixture was allowed to warm to room temperature and then stirred for 15 minutes. The mixture was then cooled to 0° C., 2-trimethysilylethoxymethyl chloride (0.360 ml) was added and the resultant mixture was stirred at room temperature for a further 64 hours. The reaction mixture was quenched by addition of saturated aqueous ammonium chloride (30 ml) and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-[N-(2-bromobenzenesulphonyl)-N-(2-trimethylsilylethoxymethyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.800 g) as a colourless oil.

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. customThe reaction mixture was quenched by addition of saturated aqueous ammonium chloride (30 ml)
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane (0-20%)

Sources & evidence

ORD record
ord-f6bd5897212b421faad3c59ec8fda220
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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