4-Toluenesulfonyl chloride → HCID 58382101, compound

HRID 1627999Notes

Reaction equation

HRID 1627999 reaction equation
[CH2:1]([C:4]1[C:5]([Cl:13])=[C:6]2[CH:12]=[CH:11][NH:10][C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3].[H-].[Na+].[S:16](Cl)([C:19]1[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>CN(C=O)C>[CH2:1]([C:4]1[C:5]([Cl:13])=[C:6]2[CH:12]=[CH:11][N:10]([S:16]([C:19]3[CH:25]=[CH:24][C:22]([CH3:23])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 58382007HCID 58382007, compound

Product 1

HCID 58382101HCID 58382101, compoundYield 111%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Allyl-4-chloro-1H-pyrrolo[2,3-b]pyridine (2.24 g, 11.6 mmol) in DMF (25 mL) was cooled to about 0° C. then treated with 60 wt % NaH (0.558 g, 13.9 mmol). The mixture was stirred for about 30 min then TsCl (2.44 g, 12.8 mmol) was added. The mixture was stirred for about 15 min at about 0° C. then warmed to rt for about 30 min. The solvents were evaporated under reduced pressure then the residue was stirred with DCM (40 mL) and saturated aqueous NaHCO3 (35 mL) for about 15 min. The layers were separated then the aqueous layer was extracted with DCM (20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 5-allyl-4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (4.0 g, 111%, crude): LC/MS (Table 2, Method a) Rt=3.18 min; MS m/z 347 (M+H)+.

Workup

  1. stirringThe mixture was stirred for about 15 min at about 0° C.
  2. customThe solvents were evaporated under reduced pressure
  3. stirringthe residue was stirred with DCM (40 mL) and saturated aqueous NaHCO3 (35 mL) for about 15 min
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with DCM (20 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5152c9a6654e4f8dbb2e5b42624191ed
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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