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

HRID 84373

Reaction equation

HRID 84373 reaction equation
[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12](I)[S:13][C:6]=12.[CH:22]([C:24]1[O:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(O)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:27]3[O:28][C:24]([CH:22]=[O:23])=[CH:25][CH:26]=3)[S:13][C:6]=12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343555-Formylfuran-2-boronic acidHCID 594576617-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine

Product 1

HCID 866351855-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)furan-2-carbaldehydeYield 84.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
65 °C

Procedure

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).

Workup

  1. customwas degassed with nitrogen for 15 min
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe cake was successively washed with water and AcOEt
  5. extractionextracted with AcOEt
  6. washThe extract was successively washed with water, saturated solution of ammonium chloride, water and brine
  7. concentrationconcentrated
  8. customabsorbed on silica gel

Sources & evidence

ORD record
ord-0d1e0d715cac49d39ed6c7ca02361e41
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Linked notes

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