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Dimethylformamide → (5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester

HRID 2193852
ノート
印刷プレビュー

反応式

HRID 2193852 の反応式
[CH2:1]([O:3][P:4]([CH2:9][S:10][C:11]1[NH:15][C:14]2[CH:16]=[C:17]([Cl:21])[C:18](I)=[CH:19][C:13]=2[N:12]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[C:22]1([C:28]#[CH:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(CC)CC.CN(C=O)C>CCOC(C)=O.[Cu]I>[CH2:1]([O:3][P:4]([CH2:9][S:10][C:11]1[NH:12][C:13]2[CH:19]=[C:18]([C:29]#[C:28][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:17]([Cl:21])=[CH:16][C:14]=2[N:15]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]
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 6228DimethylformamideHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 58422987(6-Chloro-5-iodo-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester2 回

生成物 1

HCID 58422995(5-Chloro-6-phenylethynyl-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester

試薬・触媒・溶媒 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of (6-Chloro-5-iodo-1H-benzoimidazol-2-ylsulfanylmethyl)-phosphonic acid diethyl ester (Intermediate 1, 0.4 g, 1.0 mmol), phenyl acetylene (0.26 mL, 2.0 mmol), PdCl(PPh3)2 (0.34 g, 0.050 mmol), CuI (0.018 g, 0.1 mmol), Et3N (0.96 mL, 6.94 mmol), and 10.0 mL of DMF was heated to 120° C. for 10 minutes using a microwave reactor. HPLC indicated the reaction was complete. The crude mixture was diluted with 40 mL EtOAc and washed with 3×40 mL H2O. The organic fractions were separated, combined, dried over MgSO4, and concentrated in vacuo to afford an oil. This oil was purified by MPLC to afford title compound 1-1 as clear oil.

後処理

  1. washwashed with 3×40 mL H2O
  2. customThe organic fractions were separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customThis oil was purified by MPLC

出典と根拠

ORDレコード
ord-fffab433764244fda1c96a2cb2a9e472
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329914B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート