反应 #171555

反应方程式

7-(2-fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

5-formyl-2-furanboronic acid

Na2CO3

→

aldehyde

收率 84.2%

5-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-carbaldehyde

收率 84.2%

溶剂

DME ethanol water

反应条件

后处理

1. 1
   其他was degassed with nitrogen for 15 min
2. 2
   温度to cool to room temperature
3. 3
   过滤filtered
4. 4
   洗涤The cake was successively washed with water and AcOEt
5. 5
   萃取extracted with AcOEt
6. 6
   洗涤The extract was successively washed with water, saturated solution of ammonium chloride, water and brine
7. 7
   浓缩concentrated
8. 8
   其他absorbed on silica gel

实验过程

A stirred suspension of 7-(2-fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine (24) [US 2006/0287343 A1] (5.00 g, 12.01 mmol, scheme 4)], 5-formyl-2-furanboronic acid (2.19 g, 15.19 mmol), Pd(PPh3)2Cl2 (422 mg, 0.6 mmol), Na2CO3 (8.53 g, 80.50 mmol) in a mixture of DME/ethanol/water (60 mL/40 mL/40 mL) was degassed with nitrogen for 15 min, and heated at 65° C. for five hours under nitrogen. The reaction mixture was allowed to cool to room temperature, and filtered. The cake was successively washed with water and AcOEt. The filtrate and washings were combined, extracted with AcOEt. The extract was successively washed with water, saturated solution of ammonium chloride, water and brine, and concentrated. The residue was combined with the cake, absorbed on silica gel and subjected to flash column chromatography on silica gel (eluents AcOEt/DCM: 10/90 to 20/90, then MeOH/DCM: 5/95) followed by trituration with AcOEt, to afford aldehyde 107 (3.886 g, 84% yield) as a pale clay solid. MS (m/z): 385.0 (M+H).

来源