Stannous chloride dihydrate → 4-amino-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339563Notes

Reaction equation

HRID 339563 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:28])[C:19]4[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=4)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.O.O.[Sn](Cl)Cl.C(Cl)Cl.CO>CCO>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]([NH:17][C:14]2[CH:13]=[CH:12][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:16][CH:15]=2)=[O:28])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 21226129Dichloromethane methanolHCID 58342125N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]-4-nitrobenzamide

Product 1

HCID 583420794-amino-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared as described in the Nitro Reduction section using N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]-4-nitrobenzamide (0.10 g, 0.269 mmol) and tin (II) chloride dihydrate (0.30 g, 1.34 mmol) in EtOH (15 ml) to give the title compound (0.072 g, 78%) as a pale yellow solid after work-up and flash chromatography (15:1 DCM/MeOH).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-af024a3812dd4aceb714b0aece2e2005
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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