HRID376776

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID10340

Carbonic acid sodium salt (1:2)

CNa2O3

HCID10969730

未命名化合物

HCID19359100

(4-Decyl-2,3-difluorophenyl)boronic acid

C16H25BF2O2

PRODUCTS

生成物

结构：CCCCCCCCCCc1ccc(-c2cnc(-c3ccc(OCCCCCC)nc3)nc2)c(F)c1F

HCID19359112

未命名化合物

收率 39.2%

AUXILIARIES

试剂、催化剂与溶剂

结构：c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1

催化剂HCID178418397

未命名化合物

溶剂HCID702

Ethanol

C2H6O

溶剂HCID962

Water

H2O

溶剂HCID1140

Toluene

C7H8

PROCEDURE

实验过程

The reaction of 2 mmol of 5-bromo-2-(6-hexyloxypyridin-3-yl)pyrimidine, 2 mmol of 4-decyl-2,3-difluorophenylboronic acid, 4 mmol of sodium carbonate and 0.02 mmol of tetrakis(triphenylphosphine)palladium(0) in 8 ml of toluene, 3 ml of ethanol and 3 ml of water is carried out analogously to the procedure indicated for Example 1a). The crude product is separated off by column chromatography on silica gel 60 using ethyl acetate as eluent and is recrystallized from acetonitrile, giving 0.4 g (39%) of colorless crystals, X 96 SA 127 I.

WORKUP

后处理

customThe crude product is separated off by column chromatography on silica gel 60 using ethyl acetate as eluent
customis recrystallized from acetonitrile

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-cbf17ac38a74456aad65cfc01f980d50
来源数据集: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06022492
来源说明: uspto-grants-2000_02

反应 SMILES

Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=2)=[N:6][CH:7]=1.[CH2:21]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[C:33]([F:40])[C:32]=1[F:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([C:31]1[CH:36]=[CH:35][C:34]([C:2]2[CH:3]=[N:4][C:5]([C:8]3[CH:9]=[N:10][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:13]=3)=[N:6][CH:7]=2)=[C:33]([F:40])[C:32]=1[F:41])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]