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Methyl Acrylate → (2E)-3-[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-2-propenoic acid, methyl ester

HRID 1816038
ノート
印刷プレビュー

反応式

HRID 1816038 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8].[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:22][C:5]1[CH:4]=[CH:3][C:2](/[CH:25]=[CH:24]/[C:23]([O:27][CH3:28])=[O:26])=[CH:21][C:6]=1[C:7]([NH:9][CH2:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 79213085-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

生成物 1

HCID 12988684(2E)-3-[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-2-propenoic acid, methyl ester

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

5-Bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (5 g), methyl acrylate (1.4 ml), triethylamine (2. 1 ml), palladium acetate (0.070 g) and tri-orthotolyl phosphine (0.185 g) were combined in N,N-dimethylformamide (20 ml). The mixture was heated in a sealed tube under nitrogen at 90° C. for 24 h. After cooling, the reaction mixture was partitioned between dichloromethane and dilute hydrochloric acid, the mixed phases were filtered through celite and the phases separated. The organic layer was washed with dilute hydrochloric acid and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a residue which was triturated with diethyl ether and filtered to yield the subtitled compound as an off white solid (4.1 g).

後処理

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between dichloromethane and dilute hydrochloric acid
  3. filtrationthe mixed phases were filtered through celite
  4. customthe phases separated
  5. washThe organic layer was washed with dilute hydrochloric acid and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue which
  9. customwas triturated with diethyl ether
  10. filtrationfiltered

出典と根拠

ORDレコード
ord-d6fec2b7243a4e2db62da7b983c09692
出典データセット
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06881754B2

反応ノート

読み込み中…

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