HCID 86624813, compound → HCID 55293190, compound

HRID 1641401Notes

Reaction equation

HRID 1641401 reaction equation
[N:1]([CH:4]([C:6]1[N:11]=[C:10]([CH3:12])[C:9]([F:13])=[CH:8][CH:7]=1)[CH3:5])=[N+]=[N-]>[Pd]>[F:13][C:9]1[CH:8]=[CH:7][C:6]([CH:4]([NH2:1])[CH3:5])=[N:11][C:10]=1[CH3:12]

Participants

3

Reactant 1

HCID 86624813HCID 86624813, compound

Product 1

HCID 55293190HCID 55293190, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A 250 ml round bottom flask containing 6-(1-azidoethyl)-3-fluoro-2-methylpyridine (Method 20; 567 mg, 3.15 mmol) was charged with 10% Pd/C (242 mg) and was evacuated and backfilled with H2 via a filled balloon. MeOH (6 ml) was added, and the mixture was allowed to stir at room temperature. After 1 hour, the mixture was filtered through a plug of diatomaceous earth, which was subsequently washed well with MeOH. The filtrates were concentrated to give the title compound as a pale yellow oil (404 mg, 83%). 1H NMR (400 MHz, CDCl3) δ 1.41 (d, J=6.6 Hz, 3H), 2.05 (s, 2H), 2.50 (s, 3H), 4.14 (q, J=6.6 Hz, 1H), 7.13 (d, J=3.8 Hz, 1H), 7.28 (d, J=6.6 Hz, 1H).

Workup

  1. customwas evacuated
  2. additionMeOH (6 ml) was added
  3. filtrationthe mixture was filtered through a plug of diatomaceous earth, which
  4. washwas subsequently washed well with MeOH
  5. concentrationThe filtrates were concentrated

Sources & evidence

ORD record
ord-c5d0642d0ea44b3ca9f6383c54fdbb70
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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