Trimethylsilylacetylene → Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate

HRID 2059793ノート

反応式

HRID 2059793 の反応式
Br[C:2]1[S:6][C:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:3]=1.[C:15]([Si:17]([CH3:20])([CH3:19])[CH3:18])#[CH:16].C(N(C(C)C)CC)(C)C>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:18][Si:17]([C:15]#[C:16][C:2]1[S:6][C:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:4][CH:3]=1)([CH3:20])[CH3:19]

参加物

7

反応物 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 21300388tert-butyl N-(5-bromo-1,3-thiazol-2-yl)carbamate

生成物 1

HCID 45117882Tert-butyl (5-((trimethylsilyl)ethynyl)thiazol-2-yl)carbamate収率 86%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of tert-butyl (5-bromo-1,3-thiazol-2-yl)carbamate (2.79 g, 10 mmol), ethynyltrimethylsilane (1.27 g, 13 mmol), Pd(PPh3)4 (578 mg, 0.5 mmol), CuI (143 mg, 0.75 mmol), and diisopropylethylamine (1.94 g, 15 mmol) in DMF (10 mL) was heated at 50° C. overnight under an atmosphere of N2. Upon cooling to ambient temperature, the reaction mixture was concentrated and the crude product was purified by silica gel flash chromatography (eluted with 20% EtOAc/hexanes) to give a yellow solid (2.55 g, 86%).

後処理

  1. temperatureUpon cooling to ambient temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe crude product was purified by silica gel flash chromatography (eluted with 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-fd307c3e74af4021ba605482376db853
出典データセット
uspto-grants-2012_10
特許番号
US08278307B2

反応ノート

読み込み中…