Sodium Hydroxide → HCID 57527218, compound

HRID 1671816Notes

Reaction equation

HRID 1671816 reaction equation
[CH2:1]([S:3][C:4]1[N:9]=[C:8]([CH:10]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[O:14])[C:11]#[N:12])[CH:7]=[CH:6][C:5]=1[N+:22]([O-])=O)[CH3:2].O.O.Cl[Sn]Cl.[OH-].[Na+]>CCOC(C)=O>[NH2:22][C:5]1[CH:6]=[CH:7][C:8]([CH:10]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[O:14])[C:11]#[N:12])=[N:9][C:4]=1[S:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 57527211HCID 57527211, compound

Product 1

HCID 57527218HCID 57527218, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(6-(ethylthio)-5-nitropyridin-2-yl)-3-(2-fluorophenyl)-3-oxopropanenitrile (0.40 g, 1.16 mmol, 1.0 eq.) and SnCl2.2H2O (1.35 g, 5.98 mmol, 5.2 eq.) in EtOAc (30 mL) was refluxed for 0.75 hr and cooled to room temperature. At 0° C., aqueous NaOH (1N, 15 mL) was added. The layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Silica gel chromatography using CH2Cl2:MeOH (10:0.2) as eluent afforded 2-(5-amino-6-(ethylthio)pyridin-2-yl)-3-(2-fluorophenyl)-3-oxopropanenitrile as a light brown solid (0.1933 g, 53%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acf7506a4c6c44248a9e457f4db0141e
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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