Methyl iodide → 2-(4-chloro-3-(trifluoromethyl)phenoxy)-5-(((1-methyl-5-((1-methyl-1H-indol-3-yl)methyl)-4-oxo-1,4-dihydropyrimidin-2-yl)thio)methyl)benzonitrile

HRID 474817ノート

反応式

HRID 474817 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][C:19]3[NH:20][CH:21]=[C:22]([CH2:26][C:27]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]([CH3:36])[CH:28]=4)[C:23](=[O:25])[N:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:37]([F:40])([F:39])[F:38].[CH3:41]CN(C(C)C)C(C)C.CI>C(Cl)(Cl)Cl.[Br-].[Zn+2].[Br-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][S:18][C:19]3[N:20]([CH3:41])[CH:21]=[C:22]([CH2:26][C:27]4[C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]([CH3:36])[CH:28]=4)[C:23](=[O:25])[N:24]=3)=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:37]([F:40])([F:38])[F:39]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178480220HCID 178480220、化合物

生成物 1

HCID 679535122-(4-chloro-3-(trifluoromethyl)phenoxy)-5-(((1-methyl-5-((1-methyl-1H-indol-3-yl)methyl)-4-oxo-1,4-dihydropyrimidin-2-yl)thio)methyl)benzonitrile収率 13.51%

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒HCID 6212Chloroform溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-[({5-[(1-methyl-1H-indol-3-yl)methyl]-4-oxo-1,4-dihydro-2-pyrimidinyl}thio)methyl]benzonitrile (60 mg, 0.103 mmol), DIPEA (0.054 mL, 0.310 mmol) and zinc bromide (23.26 mg, 0.103 mmol) in chloroform (2 mL) was added MeI (0.013 mL, 0.207 mmol). The mixture was heated at 60° C. for 1 h. Purification via reverse phase flash chromatography then afforded the title compound (8.3 mg, 13.51% yield). LCMS: rt=3.78 min, [M+H+]=595

後処理

  1. customPurification via reverse phase flash chromatography

出典と根拠

ORDレコード
ord-87cd714cf1ac481c8869cb2b9dca28e5
出典データセット
uspto-grants-2014_01
特許番号
US08637536B2

反応ノート

読み込み中…