8-Methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amine → 2-Ethyl-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340245Notes

Reaction equation

HRID 340245 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]2=[C:6]3[C:11](=[C:12]([NH2:14])[N:13]=[C:4]2[CH:3]=1)[N:10]=[CH:9][C:8]([CH:15]=[CH2:16])=[CH:7]3.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH2:15]([C:8]1[CH:9]=[N:10][C:11]2[C:6]([CH:7]=1)=[C:5]1[CH:17]=[CH:18][C:2]([CH3:1])=[CH:3][C:4]1=[N:13][C:12]=2[NH2:14])[CH3:16]

Participants

5

Reactant 2

HCID 582136748-Methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 582135882-Ethyl-8-methylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 8-methyl-2-vinylbenzo[f][1,7]naphthyridin-5-amine (from the previous step) in ethyl acetate/methanol (1:4, 0.05 M) was added 10% wt palladium on carbon (0.2 eq.). Hydrogen gas was introduced via a balloon, and the reaction was stirred for 3 hours. The mixture was filtered through a pad of celite and washed with dichloromethane. The filtrate was concentrated en vacuo and purified by a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 2-ethyl-8-methylbenzo[f][1,7]naphthyridin-5-amine as an offwhite solid. 1H NMR (CDCl3): δ 8.61 (d, 1H), 8.42 (d, 1H), 8.10 (d, 1H), 7.44 (s, 1H), 7.12 (dd, 1H), 6.00 (bs, 2H), 2.84 (q, 2H), 2.45 (s, 3H), 1.33 (t, 3H). LRMS [M+H]=238.1.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated en vacuo
  4. custompurified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-5d1d1e3ffcdf4c64b8c9671f100e8399
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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