반응 #171555

반응 방정식

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

5-formyl-2-furanboronic acid

Na2CO3

→

aldehyde

수율 84.2%

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

수율 84.2%

용매

DME ethanol water

반응 조건

후처리

1. 1
   기타was degassed with nitrogen for 15 min
2. 2
   온도to cool to room temperature
3. 3
   여과filtered
4. 4
   세척The cake was successively washed with water and AcOEt
5. 5
   추출extracted with AcOEt
6. 6
   세척The extract was successively washed with water, saturated solution of ammonium chloride, water and brine
7. 7
   농축concentrated
8. 8
   기타absorbed on silica gel

실험 절차

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).

출처