Dimethylamine → 2-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylethan-1-amine

HRID 1480818Notes

Reaction equation

HRID 1480818 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]2[CH:18]=[C:17]([I:19])[CH:16]=[N:15]2)(=O)=O)=CC=1.[CH3:20][NH:21][CH3:22].C1COCC1>>[I:19][C:17]1[CH:16]=[N:15][N:14]([CH2:13][CH2:12][N:21]([CH3:22])[CH3:20])[CH:18]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 89996125HCID 89996125, compound

Product 1

HCID 644311982-(4-Iodo-1H-pyrazol-1-yl)-N,N-dimethylethan-1-amineYield 89%

Procedure

2-(4-Iodo-1H-pyrazol-1-yl)ethyl 4-methylbenzenesulfonate (Preparation 58) (1.03 g, 2.63 mmol) was treated with dimethylamine in THF (2M, 10 mL, 20.00 mmol) and stirred at room temperature for 3 days. Solvents were removed under reduced pressure and the residue partitioned between DCM and saturated aqueous NaHCO3. The aqueous were extracted with DCM and the combined organic layers dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 10% MeOH in DCM to give the title compound (616 mg, 89%).

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue partitioned between DCM and saturated aqueous NaHCO3
  3. extractionThe aqueous were extracted with DCM
  4. customthe combined organic layers dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with 0 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-0f59a6da925540b6afedd712003fb605
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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