Triethylamine → Ethyl 3-[4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulen-2-yl]acrylate

HRID 389020ノート

反応式

HRID 389020 の反応式
C(N(CC)CC)C.[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=[CH2:10].C1(C)C(C(P(C(C2C(C)=CC=CC=2)=O)C(C2C(C)=CC=CC=2)=O)=O)=CC=CC=1.Br.Br[C:45]1[S:54][C:53]2[C:52](=[C:55]3[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]3)[C:51]3[CH:62]=[CH:63][CH:64]=[CH:65][C:50]=3[CH2:49][CH2:48][C:47]=2[CH:46]=1.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:61][N:58]1[CH2:59][CH2:60][C:55](=[C:52]2[C:51]3[CH:62]=[CH:63][CH:64]=[CH:65][C:50]=3[CH2:49][CH2:48][C:47]3[CH:46]=[C:45]([CH:10]=[CH:9][C:8]([O:12][CH2:13][CH3:14])=[O:11])[S:54][C:53]2=3)[CH2:56][CH2:57]1

参加物

8

反応物 5

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 19696886Tri(o-toluoyl)phosphineHCID 684884902-Bromo-4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulene hydrobromide

生成物 1

HCID 68489717Ethyl 3-[4-(1-methylpiperidin-4-ylidene)-9,10-dihydro-4H-3-thiabenzo[f]azulen-2-yl]acrylate収率 79%

試薬・触媒・溶媒 2

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

反応条件

温度
80 °C

実験手順

Triethylamine (35.5 mL, 255 mmol), ethyl acrylate (26.8 mL, 246 mmol), palladium acetate (0.4 g, 1.8 mmol), and tri(o-toluoyl)phosphine (1.5 g, 5.0 mmol) were added to a DMF (160 mL) solution of Compound 2 (9.2 g, 24.5 mmol), and the mixture was stirred overnight at 80° C. in an argon atmosphere. A saturated aqueous ammonium chloride solution was added to the reaction mixture, the product was extracted with ethyl acetate, and the organic layer was then washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvents were distilled off under a reduced pressure, and the resulting residue was then purified by column chromatography (chloroform-methanol=9:1), to give 7.6 g (79%) of the captioned compound in the form of white crystals.

後処理

  1. extractionthe product was extracted with ethyl acetate
  2. washthe organic layer was then washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvents were distilled off under a reduced pressure
  5. customthe resulting residue was then purified by column chromatography (chloroform-methanol=9:1)

出典と根拠

ORDレコード
ord-aed14948fe564fcfae3708f3279ecee8
出典データセット
uspto-grants-2013_02
特許番号
US08377967B2

反応ノート

読み込み中…