4-(2-Propyn-1-yl)morpholine → (4-{3-[3-Bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid methyl ester

HRID 548560

反応式

HRID 548560 の反応式
[CH2:1]([N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[CH3:10][O:11][C:12](=[O:34])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][C:25]2[CH:30]=[C:29]([Br:31])[CH:28]=[C:27](Br)[CH:26]=2)=[CH:17][C:16]=1[CH3:33]>CN(C=O)C.C(N(CC)CC)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>[CH3:10][O:11][C:12](=[O:34])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][C:25]2[CH:26]=[C:27]([C:3]#[C:2][CH2:1][N:4]3[CH2:9][CH2:8][O:7][CH2:6][CH2:5]3)[CH:28]=[C:29]([Br:31])[CH:30]=2)=[CH:17][C:16]=1[CH3:33]

参加物

7

反応物 2

HCID 4129414-(2-Propyn-1-yl)morpholineHCID 67157962{4-[3-(3,5-Dibromo-phenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester2 回

生成物 1

HCID 67157848(4-{3-[3-Bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid methyl ester

試薬・触媒・溶媒 4

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HCID 8471Triethylamine溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-prop-2-ynyl-morpholine (330 mg, 2.64 mmol), {4-[3-(3,5-dibromophenyl)-prop-2-ynyloxy]-2-methyl-phenoxy}-acetic acid methyl ester (206 mg, 0.44 mmol, intermediate 2), Pd(PPh3)2Cl2 (50 mg, 0.044 mmol), CuI (23 mg, 0.123 mmol) in dry DMF (2 ml) and triethylamine (2 ml) was heated in a microwave own for 30 min at 60° C. in a sealed tube. The reaction mixture was filtered through Decalite and the filtrate was evaporated. The residue was purified on column chromatography using methylene chloride/THF mixtures to give (4-{3-[3-bromo-5-(3-morpholin-4-yl-prop-1-ynyl)-phenyl]-prop-2-ynyloxy}-2-methylphenoxy)-acetic acid methyl ester in 130 mg (58%) yield.

後処理

  1. filtrationThe reaction mixture was filtered through Decalite
  2. customthe filtrate was evaporated
  3. customThe residue was purified on column chromatography

出典と根拠

ORDレコード
ord-590996a91dd44db6befdbae9d5c61c21
出典データセット
uspto-grants-2011_05
特許番号
US07943612B2

関連ノート

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