Ethanol → N-(5-(1H-pyrazol-4-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide

HRID 1036185Notes

Reaction equation

I[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=3)=[CH:13][CH:12]=2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][NH:36][CH:37]=2)O1.C(O)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:35]1[CH:34]=[C:33]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:24])[CH2:10][C:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=4)=[CH:13][CH:12]=3)=[N:6][CH:7]=2)[CH:37]=[N:36]1

Participants

Conditions

Temperature: 90 °C

Procedure

N-(5-Iodopyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide 65-2 (20 mg, 0.046 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (13.5 mg, 0.07 mmol) and Pd(PPh3)4 (5 mg, 0.004 mmol) was mixed in toluene (3 mL)/ethanol (1 mL)/Na2CO3 (2M, 1 mL). The reaction mixture was stirred at 90° C. for 10 hours. The solvent was removed by rotary evaporation and the residue was dissolved in DMSO. The inorganic salt was removed by filtration. The crude product in DMSO was purified by reverse phase HPLC to give N-(5-(1H-pyrazol-4-yl)pyridin-2-yl)-2-(4-(2-methylpyridin-4-yl)phenyl)acetamide 65 as off-white solid. MS m/z 370.2 (M+1).

Workup

customThe solvent was removed by rotary evaporation
dissolutionthe residue was dissolved in DMSO
customThe inorganic salt was removed by filtration
customThe crude product in DMSO was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-16835b93db0044fa8c54bc1dcf0718af
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546396B2

Reaction notes

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