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

HRID 1625714Notes

Reaction equation

HRID 1625714 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[C:18]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:17]2=[N:16][C:15]=3[NH2:26])=[C:5]([CH3:27])[CH:4]=1.C(O)C.[H][H]>[Pd].C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[N:13][C:14]3[C:19]([CH:20]=2)=[C:18]2[CH:21]=[CH:22][C:23]([CH3:25])=[CH:24][C:17]2=[N:16][C:15]=3[NH2:26])=[C:5]([CH3:27])[CH:4]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 581665112-((4-Methoxy-2-methylphenyl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 498381322-(4-Methoxy-2-methylphenethyl)-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-methoxy-2-methylphenyl)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 content were vacuumed followed by hydrogen flush for 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 2-(4-Methoxy-2-methylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine.hylphenethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine. 1H NMR (CDCl3): δ 8.53 (d, 1H), 8.29 (d, 1H), 8.01 (d, 1H), 7.44 (s, 1H), 7.12 (dd, 1H), 6.93 (d, 1H), 6.67 (d, 1H), 6.60 (dd, 1H), 5.93 (bs, 2H), 3.70 (s, 3H), 3.05-3.00 (dd, 2H), 2.93-2.88 (dd, 2H), 2.44 (s, 3H), 2.19 (s, 3H). LRMS [M+H]=358.2

Workup

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

Sources & evidence

ORD record
ord-5d5e5136d35d4e2b8ad0f0e3ba4564c4
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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