HRID1174756

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID1318

1,10-Phenanthroline

C12H8N2

HCID10796

Cesium carbonate

CCs2O3

HCID84834

2-(Methylsulfonyl)ethanol

C3H8O3S

结构：Cc1c(Nc2ccc(I)cc2F)ncnc1OC1CCN(C(=O)OC(C)C)CC1

HCID59856851

未命名化合物

PRODUCTS

生成物

结构：Cc1c(Nc2ccc(OCCS(C)(=O)=O)cc2F)ncnc1OC1CCN(C(=O)OC(C)C)CC1

HCID59856656

未命名化合物

收率 3%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID83717

Copper iodide (CuI2)

CuI2

CONDITIONS

反应条件

温度: 150 °C

PROCEDURE

实验过程

General procedure of coupling alcohol to aryl halides: A mixture of 4-[6-(2-fluoro-4-iodo-phenylamino)-5-methyl-pyrimidin-4-yloxy]-piperidine-1-carboxylic acid isopropyl ester (103 mg, 0.2 mmole), cesium carbonate (130 mg, 0.4 mmole), copper iodide (8 mg, 0.04 mmole), and 1,10-phenanthroline (14 mg, 0.08 mmole) in 2-methanesulfonyl-ethanol (3 mL) was heated under microwave irradiation at 150° C. for 1 hour. The crude mixture was purified by HPLC to provide Compound A95 as a yellow solid (3 mg, 3%). Exact mass calculated for C23H31FN4O6S 510.2, found 511.3 (MH+).

WORKUP

后处理

customThe crude mixture was purified by HPLC

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-ec4b05de8eaf4be79959d8d1fa3f62dd
来源数据集: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07838525B2
来源说明: uspto-grants-2010_11

反应 SMILES

[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([CH3:20])=[C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25](I)=[CH:24][C:23]=3[F:29])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH3:50][S:51]([CH2:54][CH2:55][OH:56])(=[O:53])=[O:52]>[Cu](I)I>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([O:13][C:14]2[C:19]([CH3:20])=[C:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([O:56][CH2:55][CH2:54][S:51]([CH3:50])(=[O:53])=[O:52])=[CH:24][C:23]=3[F:29])[N:17]=[CH:16][N:15]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]