O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → HCID 70980308, compound

HRID 873327Notes

Reaction equation

HRID 873327 reaction equation
[Br:1][C:2]1[C:3]([CH:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]#[N:10])=[N:4][CH:5]=[CH:6][CH:7]=1.C1(C)C=C(C)C=C(C)C=1S(O[NH2:29])(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]2[N:4]([N:10]=[C:9]([NH2:29])[C:8]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine3×HCID 70979221HCID 70979221, compound

Product 1

HCID 70980308HCID 70980308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(3-Bromo-pyridin-2-yl)-phenyl-acetonitrile (0.528 g, 1 eq) was dissolved in DCM (5 mL) and the solution cooled to 0° C. O-(Mesitylsulfonyl)hydroxylamine (0.540 g, 1 eq) was added portion-wise and the reaction was stirred at 0° C. for 2 h then stored at 4° C. for 16 h. An additional portion of 0-(mesitylsulfonyl)hydroxylamine (Intermediate 2, cf above) was added and the reaction mixture stirred at 0° C. for 2 h. The precipitate was collected by filtration and washed with pet ether 40-60 yielding the intermediate aminopyridine salt. The residue was re-dissolved in DCM/water and the aqueous was extracted with DCM (×3). The combined organics were dried and concentrated in vacuo to afford the expected product.

Workup

  1. waitthen stored at 4° C. for 16 h
  2. stirringthe reaction mixture stirred at 0° C. for 2 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with pet ether 40-60 yielding the intermediate aminopyridine salt
  5. dissolutionThe residue was re-dissolved in DCM/water
  6. extractionthe aqueous was extracted with DCM (×3)
  7. customThe combined organics were dried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8362d964f3ce441aa762f723724f294c
Source dataset
uspto-grants-2015_03
Patent number
US08975406B2

Reaction notes

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