7-Bromo-4-[1-(2,5-difluorophenyl)methylidene]-1,2,3,4-tetrahydro-[1,8]naphthyridine → 4-(2,5-Difluorobenzyl)-1,2,3,4-tetrahydro-[1,8]naphthyridine

HRID 659467Notes

Reaction equation

HRID 659467 reaction equation
Br[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[CH:12][C:13]3[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=3[F:20])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:20][C:14]1[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=1[CH2:12][CH:6]1[C:5]2[C:10](=[N:11][CH:2]=[CH:3][CH:4]=2)[NH:9][CH2:8][CH2:7]1

Participants

4

Reactant 1

HCID 767246537-Bromo-4-[1-(2,5-difluorophenyl)methylidene]-1,2,3,4-tetrahydro-[1,8]naphthyridine

Product 1

HCID 578858894-(2,5-Difluorobenzyl)-1,2,3,4-tetrahydro-[1,8]naphthyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Bromo-4-[1-(2,5-difluorophenyl)methylidene]-1,2,3,4-tetrahydro-[1,8]naphthyridine (200 mg) was dissolved in methanol (20 mL) and Pd/C (20 mg) was added. The reaction was hydrogenated at atmospheric pressure for 1.5 hours, filtered through Celite, and then concentrated under reduced pressure to give the title compound as a clear colorless oil (near quantitative yield). LCMS: m/z=261.11 (M+H+), 1H-NMR (MeOH-d4, 400 MHz) δ 1.68-1.86 (m, 2H), 2.80 (dd, J=9.0 and 13.3, 1H), 2.96 (dd, J=10.0 and 13.3 Hz, 1H), 3.02-3.12 (m, 1H), 3.34-3.41 (m, 1H), 3.46-3.55 (m, 1H), 6.44 (dd, J=5.2 and 7.2 Hz, 1H), 6.93-7.03 (m, 2H), 7.03-7.11 (m, 2H), 7.72 (dd, J=1.0 and 5.0 Hz, 1H).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f5e23679c359427ea1a9df93e5e159f2
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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