3-(Azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline → (8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methanamine

HRID 2044902Notes

Reaction equation

HRID 2044902 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])=[N+]=[N-]>C1COCC1.CO.[Pd]>[Cl:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:8]=1[N:7]=[C:6]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])[C:5]([CH2:4][NH2:1])=[CH:14]2

Participants

5

Reactant 1

HCID 577079883-(Azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)quinoline

Product 1

HCID 57707949(8-Chloro-2-(5-fluoro-2-methoxyphenyl)quinoline-3-yl)methanamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(azidomethyl)-8-chloro-2-(5-fluoro-2-methoxyphenyl)-quinoline (210.7 mg, 615 mmol) in THF 5 mL and MeOH 12 mL was added palladium, 10 wt. % on activated carbon (0.329 mmol) and placed under a medium balloon containing H2. The reaction was complete after 2 h, it was filtered (Celite™) and solvents removed.

Workup

  1. additioncontaining H2
  2. filtrationit was filtered (Celite™) and solvents
  3. customremoved

Sources & evidence

ORD record
ord-c085be5f8cf8467494e8f951dcf7cd60
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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