HCID 59424456, compound → 4-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

HRID 500866Notes

Reaction equation

HRID 500866 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([S:14]([CH3:16])=[O:15])[S:13][C:6]=12>C(O)(=O)C.[Fe]>[CH3:16][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:17]=[CH:18][C:19]([NH2:21])=[CH:20][C:2]=2[F:1])[CH:11]=1)=[O:15]

Participants

4

Reactant 1

HCID 59424456HCID 59424456, compound

Product 1

HCID 594245284-(2-(Methylsulfinyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamineYield 77.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To as solution of 233 (400 mg, 1.135 mmol) in acetic acid (10 mL) at 100° C., was added iron powder (317 mg, 5.675 mmol). The reaction mixture was stirred for 5 minutes, filtered through a celite pad and concentrated under reduced pressure. The residue was purified by column chromatography, eluent EtOAc/hexane (4:1), to afford title compound 234 (0.285 g, 69% yield) as a yellow solid. MS (m/z): 323.0 (M+1).

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography, eluent EtOAc/hexane (4:1)

Sources & evidence

ORD record
ord-4a988c3be7a644fa90b431ca2136e087
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

Loading…