Potassium Carbonate → HCID 54673361, compound

HRID 509526Notes

Reaction equation

HRID 509526 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][C:5](Br)=[CH:4][N:3]=1.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:6][C:5]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 62155529HCID 62155529, compound

Product 1

HCID 54673361HCID 54673361, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 2-amino-5-bromo-N-phenyl-pyridine-3-carboxamide (230 mg, 0.5511 mmol), 3-pyridylboronic acid (74.45 mg, 0.6057 mmol), tetrakis(triphenylphosphine) palladium(0) (31.85 mg, 0.02756 mmol) and potassium carbonate (551.5 μL of 2 M, 1.103 mmol) in dioxane (1.40 mL) was heated in the microwave at 170° C. for 10 minutes. The reaction was filtered to remove Pd residues and partitioned between EtOAc and water. The organic phase was dried (Na2SO4), filtered and concentrated and triturated with MeCN. The resultant solid was crystallised from EtOAc to give the pure product as a pale brown solid (98 mg, 43% Yield). 1H NMR (400.0 MHz, DMSO) δ 7.12 (1H, t), 7.23 (2H, brs), 7.38 (2H, t), 7.48 (1H, dd), 7.69 (1H, s), 7.72 (1H, s), 8.14 (1H, dt), 8.42 (1H, d), 8.54 (1H, dd), 8.56 (1H, d), 8.98 (1H, d), 10.28 (1H, s) ppm; MS (ES+) 290.7.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove Pd residues
  3. custompartitioned between EtOAc and water
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customtriturated with MeCN
  8. customThe resultant solid was crystallised from EtOAc

Sources & evidence

ORD record
ord-7d440e4906994761932c690e320c1749
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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