Trimethylsilylacetylene → Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine

HRID 381156ノート

反応式

HRID 381156 の反応式
Br[C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]([CH:10]2[CH2:12][CH2:11]2)[CH2:8][CH3:9])=[C:4]([CH3:15])[CH:3]=1.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.[Cu]I.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>[CH:10]1([N:7]([CH2:8][CH3:9])[CH2:6][C:5]2[CH:13]=[CH:14][C:2]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:3][C:4]=2[CH3:15])[CH2:12][CH2:11]1

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 22568961(4-Bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amine

生成物 1

HCID 22568965Cyclopropyl-ethyl-(2-methyl-4-trimethylsilanylethynyl-benzyl)-amine収率 98%

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 8471Triethylamine溶媒

反応条件

温度
70 °C

実験手順

Using General Procedure D; (4-bromo-2-methyl-benzyl)-cyclopropyl-ethyl-amnine (Intermediate 159, 620.0 mg, 2.31 mmols) in triethylamine (8 mL) was treated with copper(I)iodide (44.0 mg, 0.23 mmol) and then sparged with argon for 15 minutes. Trimethylsilylacetylene (1.04 g, 10.6 mmols) was then added followed by dichlorobis-(triphenylphosphine)palladium(II) (162.0 mg, 0.23 mmol). The resulting reaction mixture was heated to 70° C. for 5 days. The title compound (650.0 mg, 98%) was isolated by chromatography (1-4% EtOAc-hexanes).

後処理

  1. customsparged with argon for 15 minutes
  2. customThe resulting reaction mixture

出典と根拠

ORDレコード
ord-14cebf9688314c4b9e53a885fce85cc8
出典データセット
uspto-grants-2001_10
特許番号
US06303785B1

反応ノート

読み込み中…