tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate

HRID 18241

反応式

HRID 18241 の反応式
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=N[CH:7]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].[C:21]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:11]=[C:9]1[CH2:10][C:4]2[C:5](=[CH:21][CH:7]=[C:2](/[CH:14]=[CH:13]/[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:3]=2)[NH:8]1

参加物

8

反応物 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

生成物 1

HCID 66905345tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate収率 162.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 7854Propionitrile溶媒

実験手順

A solution of 5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 9.49 mmole), tert-butyl acrylate (1.8 g, 14.1 mmole), Pd(OAc)2 (0.32 g, 1.4 mmole), tri-ortho-tolylphosphine (0.57 g, 1.9 mmole), and diisopropylethylamine (4.9 mL, 28.2 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.80 g, 33%) as a light yellow solid. MS (ES) m/e 261 (M+H)+.

後処理

  1. temperatureat reflux overnight
  2. filtrationThe dark mixture was filtered through Celite®
  3. concentrationthe filtrate was concentrated

出典と根拠

ORDレコード
ord-dc079d50c56847c69bbdaca74f76ae5d
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

関連ノート

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