Sodium Hydroxide → HCID 66758161, compound

HRID 1643178Notes

Reaction equation

HRID 1643178 reaction equation
BrC1C=CC=C2C=1[N:9]([S:11](C1C=CC(OC)=CC=1)(=[O:13])=[O:12])CC2.[Br:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2C=1N[CH:29]=[CH:28]2.[C:32]([BH3-])#[N:33].[Na+].[OH-].[Na+]>C(O)(=O)C>[Br:22][CH:23]1[CH2:24][C:25]2[C:32](=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:33]1[S:11]([NH2:9])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 27570207-BromoindoleHCID 5003444Sodium cyanoborohydrideHCID 66757485HCID 66757485, compound

Product 1

HCID 66758161HCID 66758161, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Bromo-1-(4-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole (11 in scheme 2 wherein R2═OCH3): A solution of 7-bromo-1H-indole (0.30 g, 1.53 mmol) in glacial acetic acid (1.5 mL) was treated with sodium cyanoborohydride (0.14 g, 2.29 mmol) under N2 at 0° C. After aqueous sodium hydroxide solution was added to quench excess acid, the resulting mixture was then extracted with CH2Cl2 (20 mL×3). The combined organic layers were dried over MgSO4, the dried solution was filtered, and the filtrate was concentrated. The residue was dissolved in pyridine and 4-methoxyphenylsulfonyl chloride was added. The reaction mixture was refluxed overnight. The solvent was removed and the residue was purified by flash chromatography (EtOAc: n-hexane=1:2) to afford 11 (370.6 mg, 87%).

Workup

  1. customto quench excess acid
  2. extractionthe resulting mixture was then extracted with CH2Cl2 (20 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationthe dried solution was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in pyridine
  7. addition4-methoxyphenylsulfonyl chloride was added
  8. temperatureThe reaction mixture was refluxed overnight
  9. customThe solvent was removed
  10. customthe residue was purified by flash chromatography (EtOAc: n-hexane=1:2)

Sources & evidence

ORD record
ord-f2b123a9d2834c4cbb3e4a7e01cac89e
Source dataset
uspto-grants-2012_02
Patent number
US08119683B2

Reaction notes

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