Chlorotrimethylsilane → (Z)-1,3-dihydro-4-(5-hydroxy-1-pentynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 1069663ノート

反応式

HRID 1069663 の反応式
[CH2:1]([OH:6])[CH2:2][CH2:3][C:4]#[CH:5].Cl[Si](C)(C)C.Br[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1/[C:15](=[CH:23]/[C:24]1[NH:25][CH:26]=[CH:27][C:28]=1[O:29][CH3:30])/[C:16](=[O:22])[NH:17]2>CN(C=O)C.C(N(CC)CC)C>[OH:6][CH2:1][CH2:2][CH2:3][C:4]#[C:5][C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1/[C:15](=[CH:23]/[C:24]1[NH:25][CH:26]=[CH:27][C:28]=1[O:29][CH3:30])/[C:16](=[O:22])[NH:17]2

参加物

6

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 793464-Pentyn-1-olHCID 18359254(Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one2 回

生成物 1

HCID 59959882(Z)-1,3-dihydro-4-(5-hydroxy-1-pentynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

Using Method I above, 4-pentyn-1-ol (40 mg, 0.57 mmol) (Aldrich) was dissolved, under argon, in 3 mL DMF and 2 mL triethylamine, and to this solution was added chlorotrimethylsilane (0.13 mL, 1 mmol) (Aldrich). The reaction was stirred at room temperature for 1 h, at which time (Z)-4-bromo-1,3-dihydro-3-1(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (110 mg, 0.38 mmol) (Starting Material 1 supra) was added and the solution was degassed for 15 min by bubbling argon through the solution. (Ph3P)2PdCl2 (15 mg) (Aldrich) and Cul (7 mg) (Aldrich) were added and the reaction was heated at 70° C. for 14 h. The reaction mixture was then poured into 25 mL 1 N HCl and the yellow precipitate was filtered off. The product was purified via flash column chromatography to obtain (Z)-1,3-dihydro-4-(5-hydroxy-1-pentynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a yellow powder. (Yield 55 mg, 45%).

後処理

  1. additionwas added
  2. customthe solution was degassed for 15 min
  3. customby bubbling argon through the solution
  4. addition(Ph3P)2PdCl2 (15 mg) (Aldrich) and Cul (7 mg) (Aldrich) were added
  5. additionThe reaction mixture was then poured into 25 mL 1 N HCl
  6. filtrationthe yellow precipitate was filtered off
  7. customThe product was purified via flash column chromatography

出典と根拠

ORDレコード
ord-d16ab0b3783b45c5831e868dbd4c7630
出典データセット
uspto-grants-2001_06
特許番号
US06252086B1

反応ノート

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