Potassium Hydroxide → 5-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoroaniline

HRID 715091Notes

Reaction equation

HRID 715091 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[NH2:13][C:14]1[C:19]([CH:20]=O)=[CH:18][N:17]=[C:16]([Cl:22])[CH:15]=1.[OH-].[K+]>CCO.[Cl-].[Na+].O>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([CH:3]=3)[NH2:1])[C:10]([CH3:11])=[N:13]2)=[CH:18][N:17]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 454801984-Amino-6-chloropyridine-3-carbaldehydeHCID 898142011-(3-Amino-4-fluorophenyl)propan-2-one

Product 1

HCID 898155055-(7-Chloro-2-methyl-1,6-naphthyridin-3-yl)-2-fluoroanilineYield 60.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Heat a solution of 1-(3-amino-4-fluorophenyl)propan-2-one (0.34 g, 2.034 mmol), 4-amino-6-chloronicotinaldehyde (0.318 g, 2.034 mmol) and KOH (0.057 g, 1.017 mmol) in EtOH (12 mL) at 60° C. for 1 h. Cool the mixture to RT, add brine and extract with EtOAc (3×). Dry the combined organics over MgSO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (353 mg, 60%). MS (ESI) m/z: 288.1 (M+H+).

Workup

  1. extractionextract with EtOAc (3×)
  2. dry with materialDry the combined organics over MgSO4
  3. concentrationconcentrate to dryness
  4. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-b184bcb151ac4b538f91e1e978402d1d
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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