Potassium Carbonate → HCID 90403630, compound

HRID 1049363Notes

Reaction equation

HRID 1049363 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=2)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[N+:15]([C:12]1[N:11]=[CH:10][C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:26]3[CH:31]=[N:30][C:29]([NH2:32])=[CH:28][CH:27]=3)[CH:7]=2)=[CH:14][CH:13]=1)([O-:17])=[O:16]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 593227792-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine

Product 1

HCID 90403630HCID 90403630, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example A1 (0.525 g, 2.086 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (0.551 g, 2.504 mmol) in dioxane (16 mL) was sparged with Ar, treated with a solution of K2CO3 (0.577 g, 4.17 mmol) in water (4 mL) and heated at 90° C. for 1 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (3×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was treated with 60% EtOAc/Hex, sonicated and the resulting solid collected via filtration to afford 4-((6-nitropyridin-3-yl)oxy)-[2,3′-bipyridin]-6′-amine (580 mg, 90%) as a dark orange solid. 1H NMR (400 MHz, DMSO-d6): δ 8.66 (d, J=2.5 Hz, 1H), 8.58 (d, J=2.8 Hz, 1H), 8.55 (d, J=5.6 Hz, 1H), 8.40 (dd, J=8.9, 0.5 Hz, 1H), 8.06 (dd, J=8.7, 2.5 Hz, 1H), 7.96 (dd, J=8.9, 2.8 Hz, 1H), 7.61 (d, J=2.3 Hz, 1H), 7.02 (dd, J=5.6, 2.3 Hz, 1H), 6.48 (dd, J=8.7, 0.7 Hz, 1H), 6.32 (s, 2H); MS (ESI) m/z: 310.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. additionThe material was treated with 60% EtOAc/Hex
  7. customsonicated
  8. filtrationthe resulting solid collected via filtration

Sources & evidence

ORD record
ord-38c1504fb806406a952c633160c3bf26
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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