Potassium Carbonate → 6-(4-Methoxy-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid o-tolylamide

HRID 1713392Notes

Reaction equation

HRID 1713392 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[CH:11]=[N:12][N:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=12)=[O:9].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Pd].ClP(C1C=CC=CC=1C1C=CC=CC=1N(C)C)(C12CC(CC1)CC2)C12CC(CC1)CC2>[C:1]1([CH3:20])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([C:10]1[CH:11]=[N:12][N:13]2[CH:18]=[C:17]([C:26]3[CH:27]=[CH:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[CH:16]=[CH:15][C:14]=12)=[O:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 68505887HCID 68505887, compound

Product 1

HCID 166596936-(4-Methoxy-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid o-tolylamide

Reagents, catalysts & solvents 2

HCID 178482710HCID 178482710, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

6-Bromo-pyrazolo[1,5-a]pyridine-3-carboxylic acid o-tolylamide (50 mg, 0.15 mmol), 4-methoxyphenylboronic acid (27.9 mg, 0.18 mmol), chloro-[2′-(dimethylamino)-2-biphenylyl]-(dinorbornylphosphine)-palladium (4.6 mg, 7.6 μmol; Fluka, CAS # 359803-53-5) and potassium carbonate (84 mg, 0.61 mmol) are heated in 5 ml dry dioxane to 130° C. for 20 minutes in the microwave oven. The product is isolated by automated column chromatography and is dried at the high vacuum pump, yielding the title compound as a white solid.

Workup

  1. customThe product is isolated by automated column chromatography
  2. customis dried at the high vacuum pump

Sources & evidence

ORD record
ord-1cf0a0b7bcce41cd9b1aa41d26305e36
Source dataset
uspto-grants-2010_09
Patent number
US07795273B2

Reaction notes

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