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 706051노트

반응식

HRID 706051 반응식
[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]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 178480220HCID 178480220, 화합물

생성물 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)benzonitrile수율 13.51%

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 6212Chloroform용매

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온도
60 °C

실험 절차

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

후처리

  1. customPurification via reverse phase flash chromatography

출처 및 근거

ORD 기록
ord-5b5ffb056ae5474e8daa437df8f062f4
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174968B2

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