Carbonic acid sodium salt (1:2) → HCID 178418718，化合物

HRID 11818

反应方程式

HRID 11818 反应方程式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([NH:18][C:19]3[NH:20][N:21]=[C:22]([CH3:24])[CH:23]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:7]=[CH:6][C:5]([C:8]2[N:17]=[C:16]([NH:18][C:19]3[NH:20][N:21]=[C:22]([CH3:24])[CH:23]=3)[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1

参与物

7

反应物 4

HCID 10340Carbonic acid sodium salt (1:2)HCID 11776三苯基膦HCID 66827苯硼酸HCID 178418845[2-(4-bromo-phenyl)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine

产物 1

HCID 178418718HCID 178418718，化合物收率 51.4%

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 21881883Oxolane--water (1/1)溶剂

反应条件

温度
80 °C

实验过程

Method H(i). To a mixture of [2-(4-bromo-phenyl)-quinazolin-4-yl]-(5-methyl-2H-pyrazol-3-yl)-amine (196 mg, 0.51 mmol) and phenylboronic acid (75 mg, 0.62 mmol) in THF/water (1/1, 4 mL) is added Na2CO3 (219 mg, 2.06 mmol), triphenylphosphine (9 mg, 1/15 mol %) and palladium acetate (1 mg, 1/135 mol %). The mixture is heated at 80° C. overnight, the solvents are evaporated and the residue is purified by flash chromatography (gradient of CH2Cl2/MeOH) to give (2-biphenyl-4-yl-quinazolin-4-yl)-(5-methyl-2H-pyrazol-3-yl)-amine as a yellow solid (99 mg, 51%): 1H NMR (DMSO) δ 2.37 (3H, s), 6.82 (1H, s), 7.39–7.57 (4H, m), 7.73–7.87 (6H, m), 8.57 (2H, d), 8.67 (1H, d), 10.42 (1H, s), 12.27 (1H, s); MS 378.2 (M+H)+

后处理

  1. customthe solvents are evaporated
  2. customthe residue is purified by flash chromatography (gradient of CH2Cl2/MeOH)

来源与证据

ORD记录
ord-c773c44bb45845f98c56eecf02d8c1d4
来源数据集
uspto-grants-2006_08
专利号
US07098330B2

关联笔记

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