7-(2-Fluoro-4-nitrophenoxy)-2-(methylthio)thieno[3,2-b]pyridine → 4-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 1711005Notes

Reaction equation

HRID 1711005 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([S:14][CH3:15])[S:13][C:6]=12>C(O)(=O)C.[Fe]>[CH3:15][S:14][C:12]1[S:13][C:6]2[C:7](=[N:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]2[CH:16]=[CH:17][C:18]([NH2:20])=[CH:19][C:2]=2[F:1])[CH:11]=1

Participants

4

Reactant 1

HCID 594244887-(2-Fluoro-4-nitrophenoxy)-2-(methylthio)thieno[3,2-b]pyridine

Product 1

HCID 594244654-(2-(Methylthio)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To as solution of 230 (84 mg, 0.250 mmol) in acetic acid (5 mL) at 100° C., was added iron powder (0.069 g, 1.249 mmol). The reaction mixture was allowed to stir for 5 minutes, filtered through a celite pad and concentrated under reduced pressure. The residue was purified by column chromatography, eluent DCM/MeOH (50:1), to afford title compound 231 (61 mg, 80% yield) as yellow oil. MS (m/z): 307.1 (M+1).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography, eluent DCM/MeOH (50:1)

Sources & evidence

ORD record
ord-083cd07d37b74d03bd81ba3ee6136edc
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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