Sodium hydride → N-(1-(3-Chlorophenyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

HRID 1643888Notes

Reaction equation

HRID 1643888 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].[H-].[Na+].C[Si](C)(C)CCO[CH2:30][Cl:31]>CN(C=O)C>[Cl:31][C:30]1[CH:11]=[C:12]([N:9]2[C:10]3[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:12][CH:11]=3)[CH2:6][CH:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:8]2)[CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 17759418N-(6-Cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Product 1

HCID 66757636N-(1-(3-Chlorophenyl)-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamideYield 146.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 153A (627 mg, 2 mmol) in DMF (5 mL) at RT was added NaH (96 mg, 2.4 mmol) in portions. After addition, the reaction was stirred at RT for 30 min, and then 2-(trimethylsilyl)ethoxymethyl chloride (0.37 mL, 2.10 mmol) was added dropwise. After addition, the reaction was stirred at RT for 1 h, then quenched carefully with water. The mixture was extracted with EtOAc (3×30 mL), and the combined extracts washed with brine, dried (Na2SO4), and concentrated. The resulting residue was chromatographed (silica gel) eluting with EtOAc (0-60%) in hexane to give the title compound as a white powder (620 mg, 70%).

Workup

  1. additionAfter addition
  2. additionAfter addition
  3. stirringthe reaction was stirred at RT for 1 h
  4. customquenched carefully with water
  5. extractionThe mixture was extracted with EtOAc (3×30 mL)
  6. washthe combined extracts washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe resulting residue was chromatographed (silica gel)
  10. washeluting with EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-efea2754d1e241f1aaea78f72351be55
Source dataset
uspto-grants-2012_02
Patent number
US08119808B2

Reaction notes

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