HRID1792609

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID522689

Potassium fluoride

HCID2734215

2-(Di-tert-butylphosphino)biphenyl

C20H27P

结构：CCOC(=O)c1ccc(-c2ncnc3ccc(Cl)cc23)cc1F

HCID22031224

未命名化合物

结构：OB(O)c1cnn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c1

HCID22031737

[1-(Triphenylmethyl)-1H-pyrazol-4-yl]boronic acid

C22H19BN2O2

PRODUCTS

生成物

结构：CCOC(=O)c1ccc(-c2ncnc3ccc(-c4cnn(C(c5ccccc5)(c5ccccc5)c5ccccc5)c4)cc23)cc1F

HCID22031192

未命名化合物

收率 70.1%

AUXILIARIES

试剂、催化剂与溶剂

催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

溶剂HCID962

Water

H2O

2 次

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

0.64 g ethyl 4-(6-chloroquinazolin-4-yl)-2-fluorobenzoate (compound in Production Example 385), 1.02 g 1-trityl-1H-4-pyrazolylboronic acid, 0.34 g potassium fluoride, 43 mg palladium (II) acetate, 0.11 g 2-(di-t-butylphosphino)biphenyl, 20 mL N,N-dimethylformamide and 2 mL water were heated at 70° C. for 24 hours under nitrogen atmosphere. Water was added thereto, the reaction solution was filtered, and crystals collected by filtration were washed with water. The crystals were dissolved in dichloromethane, washed with water and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by NH silica gel column chromatography (hexane/ethyl acetate), to give 0.82 g of the title compound (pale yellow crystals).

WORKUP

后处理

filtrationthe reaction solution was filtered
filtrationcrystals collected by filtration
washwere washed with water
dissolutionThe crystals were dissolved in dichloromethane
washwashed with water
dry with materialdried over sodium sulfate
customThe solvent was evaporated
customthe residue was purified by NH silica gel column chromatography (hexane/ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-a7c568d94a0f4e84ae663770a21c8249
来源数据集: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07074801B1
来源说明: uspto-grants-2006_07

反应 SMILES

Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([F:23])[CH:13]=1.[C:24]([N:43]1[CH:47]=[C:46](B(O)O)[CH:45]=[N:44]1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[F-].[K+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CN(C)C=O>[F:23][C:14]1[CH:13]=[C:12]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:46]4[CH:45]=[N:44][N:43]([C:24]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)[CH:47]=4)[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:22]=[CH:21][C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]