3-Aminopyridine → HCID 66599414, compound

HRID 2410717Notes

Reaction equation

HRID 2410717 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][CH:21]=[C:20]([NH2:24])[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:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)=[C:3]([C:16]#[N:17])[CH:4]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 23665647Potassium tert-butoxideHCID 66599556HCID 66599556, compound

Product 1

HCID 66599414HCID 66599414, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-fluoro-3′-methoxybiphenyl-3-carbonitrile (0.60 g, 2.64 mmol, Example 203A) in DMSO (4 mL) was added pyridine-3-amine (0.27 g, 2.90 mmol) and KOtBu (0.15 g, 1.38 mmol). The reaction stirred under nitrogen at room temperature 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-3-ylamino)biphenyl-3-carbonitrile. MS (ESI) m/z 302.2 (M+H). 1H NMR (MeOD) d ppm 8.43 (1H, d, J=2.75 Hz), 8.19 (1H, dd, J=4.88, 1.22 Hz), 7.91 (1H, d, J=2.14 Hz), 7.81 (1H, dd, J=8.70, 2.29 Hz), 7.56-7.73 (1H, m), 7.32-7.47 (3H, m), 7.11-7.23(2H, m), 6.94(1H, dd, J=8.24, 2.44 Hz), 3.87 (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-c8a028946da74e71ae8812791cd17802
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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