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

HRID 1261306Notes

Reaction equation

HRID 1261306 reaction equation
[F:1][C:2]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[S:13][C:6]=12>C(O)(=O)C.[Fe]>[CH3:17][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:18]=[CH:19][C:20]([NH2:22])=[CH:21][C:2]=2[F:1])[CH:11]=1)(=[O:15])=[O:16]

Participants

4

Reactant 1

HCID 594244607-(2-Fluoro-4-nitrophenoxy)-2-(methylsulfonyl)thieno[3,2-b]pyridine

Product 1

HCID 594245404-(2-(Methylsulfonyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 48.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 236 (45 mg, 0.122 mmol) in acetic acid (4 mL) at 100° C., was added iron powder (34 mg, 0.611 mmol). The reaction mixture was stirred for 5 minutes, filtered through a celite pad and concentrated under reduced pressure to afford title compound 237 (20 mg, 48% yield, crude) as a yellow oil that was used in the next step without further purification. MS (m/z): 339.0 (M+1).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-529943593a914953afc4eefd9e92cec1
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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