5-Fluoropyridine-3-carbaldehyde → HCID 66693428, compound

HRID 1048998Notes

Reaction equation

HRID 1048998 reaction equation
[NH2:1][C:2]1[C:9]([NH:10][CH3:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:12])[CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([CH:20]=O)[CH:17]=[N:18][CH:19]=1.OOS([O-])=O.[K+]>CN(C=O)C.O.C([O-])([O-])=O.[K+].[K+]>[F:12][C:4]1[C:5]([C:6]#[N:7])=[CH:8][C:9]2[N:10]([CH3:11])[C:20]([C:16]3[CH:17]=[N:18][CH:19]=[C:14]([F:13])[CH:15]=3)=[N:1][C:2]=2[CH:3]=1

Participants

7

Reactant 3

HCID 141411595-Fluoropyridine-3-carbaldehydeHCID 23707502Potassium hydroxy sulfiteHCID 66684554HCID 66684554, compound

Product 1

HCID 66693428HCID 66693428, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 11430Potassium CarbonateSolvent

Procedure

To a solution of 4-amino-2-fluoro-5-methylamino-benzonitrile (0.15 g, 0.00090 mol) and 5-Fluoro-pyridine-3-carbaldehyde (0.11 g, 0.0090 mol) in DMF (5 mL) and H2O (2 mL) was added OXONE® monopersulphate (0.19 g, 0.0012 mol). The reaction mixture was stirred at room temperature for 5 h, and was diluted with 10% K2CO3 solution to PH˜8-10 and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to afford the crude compound, which was purified by column chromatography to obtain title compound 5-fluoro-2-(5-fluoropyridin-3-yl)-1-methyl-1H-benzimidazole-6-carbonitrile (398) as a brown solid. C14H8F2N4; 1H NMR (400 MHz, DMSO-d6) δ 8.96 (s, 1H), 8.83 (d, J=2.4 Hz, 1H), 8.47 (d, 5.4 Hz, 1H), 8.29 (d, J=9.6 Hz, 1H), 7.88 (d, J=9.6 Hz, 1H), 3.98 (s, 3H); MS (M+1): 271.1. HPLC purity: 99.44%.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto afford the crude compound, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-0a6a03619cbd4ec396996092a36f69d7
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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