HCID 70970401, compound → HCID 86677131, compound

HRID 1771877Notes

Reaction equation

HRID 1771877 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C@@H:10]([N:12]=[N+]=[N-])[CH3:11]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C@@H:10]([NH2:12])[CH3:11]

Participants

4

Reactant 1

HCID 70970401HCID 70970401, compound

Product 1

HCID 86677131HCID 86677131, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S)-2-(2-chloro-5-fluorophenyl)-1-methylethyl azide (1.10 g, 5.15 mmol) in 100 mL of EtOAc was added Pd/C (300 mg of 10% Pd) and the mixture was hydrogenated under hydrogen balloon for 30 min. The catalyst was removed by filtration through celite, then passed through silicagel plug eluting first with EtOAc (40 mL), then MeOH/EtOAc/NH4OH 20:75:5 (120 mL). The fraction with product was evaporated to give (1S)-2-(2-chloro-5-fluorophenyl)-1-methylethylamine (721 mg, 67%) as pale yellow oil. ESI-MS: m/z (MH+) 188.3. 1H NMR (300 MHz, CDCl3): δ 7.30 (m, 1H), 6.86-6.97 (m, 2H), 3.26 (m, 1H), 2.66-2.84 (m, 2H), 1.40 (s, 2H), 1.15 (d, J=6.42 Hz, 3H).

Workup

  1. customfor 30 min
  2. customThe catalyst was removed by filtration through celite
  3. washeluting first with EtOAc (40 mL)
  4. customThe fraction with product was evaporated

Sources & evidence

ORD record
ord-99eae99f710c4285bc1e7cc0d2aa24e5
Source dataset
uspto-grants-2016_02
Patent number
US09249147B2

Reaction notes

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