Ethanol → 2-(4-Ethoxyphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 340259Notes

Reaction equation

HRID 340259 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[C:19]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]2=[N:17][C:16]=3[NH2:27])=[CH:6][CH:5]=1)[CH3:2].C(O)C>[Pd].C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[C:19]2[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]2=[N:17][C:16]=3[NH2:27])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 668749052-((4-Ethoxyphenyl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 582137602-(4-Ethoxyphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added 2-((4-ethoxyphenyl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine (from the previous step) (1 eq.) with a stirring bar. Ethanol and methylene chloride (1:2, 0.2 M) were added, followed by palladium in carbon (activated powder, wet, 10% on carbon, 0.1 eq.). The contents were degassed under vacuum followed by hydrogen flush (three times). The reaction mixture was stirred vigorously under hydrogen balloon at room temperature overnight. Afterwards the reaction mixture was filtered through a celite pad, and the celite pad was washed subsequently with methylene chloride and EtOAc until the filtrate had no UV absorption. Combined organic washes were concentrated. Flash chromatography (silica gel, 0-50% EtOAc in CH2Cl2) afforded the product as a yellow solid. Further recrystallization using toluene afforded product 2-(4-ethoxyphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine as a white fine crystal. 1H NMR (CDCl3): δ 8.52 (d, 1H), 8.30 (d, 1H), 8.10 (d, 1H), 7.46 (s, 1H), 7.12 (dd, 1H), 7.06 (d, 2H), 6.75 (d, 2H), 5.95 (bs, 2H), 3.93 (q, 2H), 3.11-3.05 (dd, 2H), 2.95-2.90 (dd, 2H), 2.44 (s, 3H), 1.33 (t, 3H). LRMS [M+H]=358.2

Workup

  1. customThe contents were degassed under vacuum
  2. customflush (three times)
  3. filtrationAfterwards the reaction mixture was filtered through a celite pad
  4. washthe celite pad was washed subsequently with methylene chloride and EtOAc until the filtrate
  5. customno UV absorption
  6. concentrationCombined organic washes were concentrated

Sources & evidence

ORD record
ord-4ef103a26e8044db8084df9be2d3eade
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

Loading…