4-Aminopyridine → HCID 66599397, compound

HRID 2410716Notes

Reaction equation

HRID 2410716 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[CH:4][C:3]=1[C:16]#[N:17].[N:18]1[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=1.CC([O-])(C)C.[K+]>CS(C)=O>[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:24][C:21]3[CH:22]=[CH:23][N:18]=[CH:19][CH:20]=3)=[C:3]([C:16]#[N:17])[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 23665647Potassium tert-butoxideHCID 66599556HCID 66599556, compound

Product 1

HCID 66599397HCID 66599397, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-fluoro-3′-methoxybiphenyl-3-carbonitrile (0.50 g, 2.20 mmol) in DMSO (4 mL) was added pyridine-4-amine (0.23 g, 2.42 mmol) and KOtBu (0.15 g, 1.38 mmol). The reaction stirred under nitrogen at room temperature for 12 h. The reaction mixture was partitioned between water and ethyl acetate, the layers were separated, the organics were washed with water, brine solution, dried over Na2SO4 and concentrated to give the crude product. The crude material was purified by silica gel column chromatography (DCM/(2M)NH4-MeOH=100/0−95/5) to afford 0.53 g of 3′-methoxy-4-(pyridine-4-ylamino)biphenyl-3-carbonitrile. MS (ESI) m/z 302.2 (M+H). 1H NMR MeOD) d ppm 8.24 (2H, d, J=6.41 Hz), 8.01 (1H, d, J=2.44 Hz), 7.93 (1H, dd, J=8.70, 2.29 Hz), 7.61 (1H, d, J=8.55 Hz), 7.40 (1H, t, J=7.93 Hz), 7.17-7.30 (2H, m), 6.92-7.05 (3H, m), 3.88 (3H, s).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe layers were separated
  3. washthe organics were washed with water, brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThe crude material was purified by silica gel column chromatography (DCM/(2M)NH4-MeOH=100/0−95/5)

Sources & evidence

ORD record
ord-d3c6e6d9a88b4e299a9297de489600e6
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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