Ethanol → 2-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

HRID 1259124Notes

Reaction equation

HRID 1259124 reaction equation
N1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[C:11][C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[C:19]3[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]3=[N:17][C:16]=4[NH2:27])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([OH:30])C.[H][H]>[Pd].C(Cl)Cl>[O:30]1[C:9]2[CH:8]=[CH:7][C:6]([CH2:10][CH2:11][C:12]3[CH:13]=[N:14][C:15]4[C:20]([CH:21]=3)=[C:19]3[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:18]3=[N:17][C:16]=4[NH2:27])=[CH:5][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 702EthanolHCID 668930492-((1H-indol-5-yl)ethynyl)-8-methylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 442314112-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added 2-((1H-indol-5-yl)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-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-8-methylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (CDCl3): δ 8.54 (d, 1H), 8.34 (d, 1H), 8.28 (s, 1H), 7.99 (d, 1H), 7.64-7.56 (m, 1H), 7.50-7.35 (m, 1H), 7.24 (d, 1H), 7.12 (t, 1H), 7.08 (dd, 1H), 6.92 (dd, 1H), 6.41 (s, 1H), 6.01 (bs, 2H), 3.16-3.12 (m, 2H), 3.10-3.05 (m, 2H), 2.43 (s, 3H). LRMS [M+H]=353.2

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-bb69f8c363f5438fa3804f85f9cc695a
Source dataset
uspto-grants-2013_06
Patent number
US08466167B2

Reaction notes

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