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HRID1698078

反应详情

EQUATION

反应方程式

HRID 1698078 反应方程式

REACTANTS

反应物

5
Dimethylformamide 分子结构式
HCID6228

Dimethylformamide

C3H7NO

Ethyl Acetate 分子结构式
HCID8857

Ethyl Acetate

C4H8O2

Potassium Carbonate 分子结构式
HCID11430

Potassium Carbonate

CK2O3

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine 分子结构式
HCID2756555

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

C11H17BN2O2

2-Bromo-6-methoxybenzothiazole 分子结构式
HCID11218765

2-Bromo-6-methoxybenzothiazole

C8H6BrNOS

PRODUCTS

产物

1
HCID 24803565 分子结构式
HCID24803565

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

1
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) 分子结构式
催化剂HCID178418228

Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)

C34H28Cl2FeP2Pd

CONDITIONS

反应条件

温度
80 °C

PROCEDURE

实验过程

A mixture of 2-bromo-6-methoxy-benzothiazole (1.14 g), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (1.23 g, 1.2 eq.), Pd(dppf)Cl2*DCM (170 mg, 0.05 eq.) and 2.0 M aq. K2CO3 (10 ml, 4 eq.) in DMF (20 ml) was heated at 80° C. for 2 h under argon while stirring. Ethyl acetate (200 ml) was subsequently added before concentrating the sol. onto diatomaceous earth in vacuo. Purification by flash chromatography (DCM:methanol, 99:1 to 95:5) provided the title compound (730 mg) as a yellow solid. 1H NMR δ 8.56 (d, 1H) 7.96 (dd, 1H) 7.82 (d, 1H) 7.64 (d, 1H) 7.07 (dd, 1H) 6.67 (br. s, 2H) 6.55 (d, 1H) 3.83 (s, 3H); MS m/z (M+H) 258.1.

WORKUP

后处理

  1. concentrationbefore concentrating the sol. onto diatomaceous earth in vacuo
  2. customPurification by flash chromatography (DCM:methanol, 99:1 to 95:5)