Diisopropylethylamine → (E)-N-Methyl-N-(3-methyl-1H-inden-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 1825702Notes

Reaction equation

HRID 1825702 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH3:13][N:14]([CH2:19][C:20]1[CH2:21][C:22]2[C:27]([C:28]=1[CH3:29])=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15](=[O:18])[CH:16]=[CH2:17].CCN(C(C)C)C(C)C>C(#N)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:13][N:14]([CH2:19][C:20]1[CH2:21][C:22]2[C:27]([C:28]=1[CH3:29])=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15](=[O:18])/[CH:16]=[CH:17]/[C:2]1[CH:11]=[N:10][C:9]2[NH:8][C:7](=[O:12])[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 110963256-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-oneHCID 22138221N-methyl-N-(3-methyl-1H-inden-2-ylmethyl)acrylamide

Product 1

HCID 22138222(E)-N-Methyl-N-(3-methyl-1H-inden-2-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamideYield 41%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7854PropionitrileSolvent

Procedure

A mixture of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.096 g, 0.42 mmole), from Preparation 3, and N-methyl-N-(3-methyl-1H-inden-2-ylmethyl)acrylamide (0.141 g, 0.62 mmole) in propionitrile (10 mL) was treated with (i-Pr)2NEt (0.15 mL, 0.08 mmole), palladium acetate (0.014 g, 0.062 mmole), and (o-tolyl)3P (0.025 g, 0.08 mmole), and the resulting mixture was heated at gentle reflux. After 18 hr, the reaction was cooled, filtered through celite®, and concentrated. Flash chromatography on silica gel (2% MeOH/CH2Cl2) gave the title compound (0.06 g, 41%) as a glassy solid: MS (ES) m/e 374.2 (M+H)+. Anal. Calcd for C23H23N3O2.1.25 H2O: C, 69.76; H, 6.41; N, 10.61. Found: C, 69.86; H, 6.67; N, 10.51.

Workup

  1. temperaturethe resulting mixture was heated at gentle reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered through celite®
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc43712c245b465faa4ca02ec928de14
Source dataset
uspto-grants-2006_05
Patent number
US07048926B2

Reaction notes

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