2-(5-(Diethoxymethyl)pyridin-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine → 4-(2-(5-(Diethoxymethyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 1047437Notes

Reaction equation

HRID 1047437 reaction equation
[CH2:1]([O:3][CH:4]([O:31][CH2:32][CH3:33])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[O:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[F:30])[CH:12]=2)=[N:9][CH:10]=1)[CH3:2]>CCO.[Pd]>[CH2:32]([O:31][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:19][C:18]3[C:13](=[N:14][CH:15]=[CH:16][C:17]=3[O:20][C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=3[F:30])[CH:12]=2)=[N:9][CH:10]=1)[CH3:33]

Participants

4

Reactant 1

HCID 579672812-(5-(Diethoxymethyl)pyridin-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 579672714-(2-(5-(Diethoxymethyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineYield 52%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The intermediate 51 (0.29 g, 0.62 mmol) was solubilized in EtOH (100 mL) and palladium on charcoal 10% (0.075 g) was added. The reaction mixture was stirred overnight under hydrogen atmosphere, filtered through a celite pad and the filtrate was concentrated under reduce pressure. The residue was purified by column chromatography with 60-80% EtOAc in hexanes to afford intermediate 52 (0.14 g, 52% yield) as a colorless solid. MS (m/z): 440.1 (M+H).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by column chromatography with 60-80% EtOAc in hexanes

Sources & evidence

ORD record
ord-1b0ac799f53142e8a49363ad098697b8
Source dataset
uspto-grants-2013_10
Patent number
US08569503B2

Reaction notes

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