HCID 68157994, compound → HCID 68157554, compound

HRID 243172Notes

Reaction equation

HRID 243172 reaction equation
[F:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:4]([NH:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-])=O)=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:4]([NH:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([NH2:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68157994HCID 68157994, compound

Product 1

HCID 68157554HCID 68157554, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of (3-fluoro-6-nitro-2-pyridin-2-yl-phenyl)-(2-methoxyethyl)amine (414 mg, 1.4 mmol) in EtOAc (5 mL) was added to a slurry of palladium on carbon (10% by wt, 41 mg) in EtOAc (5 mL) under nitrogen. The reaction mixture was stirred at RT under an atmosphere of hydrogen for 4 h. The mixture was filtered through Celite® and the filtrate concentrated in vacuo to give the title compound as a yellow oil (382 mg, 99%). LCMS (Method C): RT 1.92 min [M+H]+ 262. 1H NMR (CDCl3, 400 MHz): δ 8.72 (1H, ddd, J=5.0, 2.0, 1.0 Hz), 7.77, (1H, ddd, J=8.0, 8.0, 2.0 Hz), 7.60-7.56 (1H, m), 7.26 (1H, ddd, J=7.5, 5.0, 1.0 Hz), 6.73-6.66 (2H, m), 5.67 (1H, bs), 3.86 (2H, bs), 3.18-3.16 (2H, m), 3.01 (3H, s), 2.96-2.93 (2H, m)

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8cf489bb3d384ea7bcf36b4e4b06d98d
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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