HCID 67313236, compound → HCID 67313485, compound

HRID 1890345Notes

Reaction equation

HRID 1890345 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:12]([N+:23]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCOCC1.[Ni]>[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:12]([NH2:23])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67313236HCID 67313236, compound

Product 1

HCID 67313485HCID 67313485, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-(benzyloxy)-N-(2-fluorophenyl)-3-nitropyridin-2-amine (2.00 g, 5.89 mmol) in dioxane (100 mL) was added Raney nickel (346 mg, 5.89 mmol). The mixture was stirred under hydrogen at room temperature for 12 h, filtered through Celite® and concentrated to give 6-(benzyloxy)-N2-(2-fluorophenyl)pyridin-2,3-diamine as an oil. The residual oil was dissolved in DCM (50 mL) and CDI (629 mg, 3.88 mmol) was added. After stirring at room temperature for 12 h the mixture was concentrated and purified by column chromatography to give the title compound (643 mg). LCMS m/z=336.4 [M+H]+.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-202fec03be004a42bf1dec6a14e85cf6
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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