Stannous chloride dihydrate → 3-(2-fluoroethoxy)-4-{(E)-2-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]ethenyl}aniline

HRID 339599Notes

Reaction equation

HRID 339599 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]4[CH:27]=3)=[CH:14][CH:13]=2)=[C:6]([O:28][CH2:29][CH2:30][F:31])[CH:5]=1)([O-])=O.O.O.[Sn](Cl)Cl.CCOC(C)=O.C(Cl)Cl>CCO>[F:31][CH2:30][CH2:29][O:28][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1/[CH:10]=[CH:11]/[C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:19]=[C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]3[CH:27]=2)=[CH:16][CH:17]=1)[NH2:1]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21226138Dichloromethane ethylacetateHCID 583420032-(4-{(e)-2-[4-Nitro-2-(2-fluoroethoxy)phenyl]ethenyl}phenyl)-6-methylimidazo[1,2-a]pyridine

Product 1

HCID 583421653-(2-fluoroethoxy)-4-{(E)-2-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]ethenyl}anilineYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using 2-(4-{(E)-2-[4-nitro-2-(2-fluoroethoxy)phenyl]ethenyl}phenyl)-6-methylimidazo[1,2-a]pyridine (81 mg, 0.194 mmol) and tin (II) dichloride dihydrate (219 mg, 0.970 mmol) in EtOH (12 ml) to give the title compound (36 mg, 48%) as an orange solid after work-up and flash chromatography (2:1 EtOAc/DCM).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3c6f488df62d464c94fbf182900e02e0
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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