Triethylamine → Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate

HRID 24140

反応式

HRID 24140 の反応式
[CH2:1]([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12]C2C=C3C(=CC=2)N(C2CC2)CCC3(C)C)=[CH:7][CH:6]=1)C.[CH3:29][O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=1.[CH2:41](N(CC)CC)[CH3:42]>[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>[CH3:29][O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]3([O:3][CH3:1])[CH2:42][CH2:41]3)=[CH:10][CH:9]=2)=[CH:35][CH:34]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 10378700Methyl 4-Iodophenylacetate2 回HCID 695488784-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-benzoic acid ethyl ester2 回

生成物 1

HCID 86585921Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate収率 78%

試薬・触媒・溶媒 2

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

実験手順

Using General Procedure F; 1-ethynyl-4-(1-methoxycyclopropyl)-benzene (Intermediate 61, 120.0 mg, 0.56 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 154.0 mg, 0.56 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (35.0 mg, 0.19 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (130 mg, 0.19 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-8% EtOAc—hexanes) afforded 140.0 mg (78%) of the title compound as an orange solid.

後処理

  1. customsparged with argon for 5 minutes

出典と根拠

ORDレコード
ord-e5c46863350e440095e86e1636b8d707
出典データセット
uspto-grants-2005_02
特許番号
US06855512B2

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