6-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid → 6-(3-Chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid

HRID 2047702Notes

Reaction equation

HRID 2047702 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]([CH3:21])([CH:19]=[CH2:20])[C:16]3[N:15]=[C:14]([C:22]([OH:24])=[O:23])[CH:13]=[CH:12][C:11]=3[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]>CO.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:18][C:17]([CH2:19][CH3:20])([CH3:21])[C:16]3[N:15]=[C:14]([C:22]([OH:24])=[O:23])[CH:13]=[CH:12][C:11]=3[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 565916986-(3-Chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid

Product 1

HCID 565916996-(3-Chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acidYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The mixture solution of 6-(3-chloro-4-fluoro-phenyl)-8-methyl-8-vinyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid (100 mg, 0.3 mmol) and 10% palladium on active carbon (30 mg) in methanol (50 mL) was stirred at room temperature under hydrogen (14 psi) for 8 hours. The catalyst was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo and purified by preparative HPLC to afford 6-(3-chloro-4-fluoro-phenyl)-8-ethyl-8-methyl-5,6,7,8-tetrahydro-[1,5]naphthyridine-2-carboxylic acid (30 mg, 30%) as a yellow oil. MS (ESI+) [(M+H)+] 349.2.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-cef6b1074efb4573b8b8588bddd856d0
Source dataset
uspto-grants-2013_11
Patent number
US08592594B2

Reaction notes

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