Triethylamine → Cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amine

HRID 1765823ノート

反応式

HRID 1765823 の反応式
Br[C:2]1[CH:3]=[C:4]([N:8]([CH:10]2[CH2:12][CH2:11]2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22].C(OCC)(=O)C>CCCCCC.[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:8]([CH3:9])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:3]=2)[CH2:12][CH2:11]1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 21107154(3-Bromo-phenyl)-cyclopropyl-methyl-amine2 回

生成物 1

HCID 57424251Cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amine収率 84%

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 8058Hexane溶媒

実験手順

Following General Procedure D and using (3-bromo-phenyl)-cyclopropyl-methyl-amine (Intermediate 113, 0.056 g, 0.25 mmol), triethyl amine (3 mL), copper(I)iodide (0.025 g, 0.13 mmol), trimethylsilyl acetylene (2.5 mL, 17.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.065 g, 0.09 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 1.5% ethyl acetate in hexane as the eluent, the title compound (0.051 g, 84%) was obtained.

出典と根拠

ORDレコード
ord-6129dfafc90d4ddab74a71403847e47d
出典データセット
uspto-grants-2007_06
特許番号
US07226951B2

反応ノート

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