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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 2112707
ノート
印刷プレビュー

反応式

HRID 2112707 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 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)acrylamide収率 41%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 7854Propionitrile溶媒

実験手順

A mixture of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (0.096 g, 0.42 mmole), from Preparation 15, 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 C23H23N3O2.1.25H2O: C, 69.76; H, 6.41; N, 10.61. Found: C, 69.86; H, 6.67; N, 10.51.

後処理

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

出典と根拠

ORDレコード
ord-8a4dae9e207c442f92d47d3564d1b0ac
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07524843B2

反応ノート

読み込み中…

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