Triethylamine → 2-(5-Fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetamide

HRID 1778990ノート

反応式

HRID 1778990 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([NH2:12])=[O:11].F[B-](F)(F)F.[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].CCN(CC)CC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[C:3]([CH2:9][C:10]([NH2:12])=[O:11])[CH:4]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 26255TetrafluoroborateHCID 66111TrimethylsilylacetyleneHCID 867126532-(2-Bromo-5-fluorophenyl)acetamide

生成物 1

HCID 867126522-(5-Fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetamide

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

Under inert conditions a suspension of 2-(2-bromo-5-fluorophenyl)acetamide (A33) (0.242 g, 1.04 mmol), PdCl2(PPh3)2 (0.037 g, 0.052 mmol), t-Bu3PH.BF4 (0.015 g, 0.052 mmol), CuI (0.010 g, 0.052 mmol) and (trimethylsilyl)acetylene (0.177 mL, 1.25 mmol) in anhydrous DMF (9 mL) was degassed with nitrogen for 10 minutes. Et3N (3 mL) was added and the resulting mixture was stirred at 65° C. under nitrogen for 16 hours. The volatiles were removed under reduced pressure, then the residue adsorbed onto silica gel and purified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.) to give the title compound A34 as a tan coloured solid (0.242 g, 93%); 1H NMR (400 MHz, d6-DMSO) δ 7.46 (dd, J=8.6, 5.9 Hz, 1H), 7.38 (s, 1H), 7.15 (dd, J=10.0, 2.7 Hz, 1H), 7.08 (td, J=8.6, 2.7 Hz, 1H), 6.99 (s, 1H), 3.60 (s, 2H), 0.23 (s, 9H).

後処理

  1. customThe volatiles were removed under reduced pressure
  2. custompurified by column chromatography (Biotage Isolera, SiO2 cartridge, 0-50% EtOAc in petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-d288641dc7ba409d92b63bc374f9874e
出典データセット
uspto-grants-2016_02
特許番号
US09266864B2

反応ノート

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