Water → 3-(3-amino-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-cyclopropyl-4-methylbenzamide

HRID 643670Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([NH2:11])=[N:9][N:10]=[C:4]2[CH:3]=1.[CH:12]1([NH:15][C:16](=[O:33])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19](B3OC(C)(C)C(C)(C)O3)[CH:18]=2)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCO>[NH2:11][C:8]1[N:5]2[CH:6]=[CH:7][C:2]([C:19]3[CH:18]=[C:17]([CH:22]=[CH:21][C:20]=3[CH3:23])[C:16]([NH:15][CH:12]3[CH2:13][CH2:14]3)=[O:33])=[CH:3][C:4]2=[N:10][N:9]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-bromo-[1,2,4]triazolo[4,3-a]pyridin-3-amine (0.202 g, 0.95 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.358 g, 1.2 mmol), sodium carbonate (0.439 g, 4.1 mmol) and trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.057 g, 0.081 mmol) in 7 μL of DME/3 mL of H2O/2 mL of EtOH was heated at 80° C. After 2.5 h, the reaction mixture was cooled to 25° C., evaporated onto silica gel and purified by flash column chromatography eluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97) to give the title compound as a tan amorphous solid. MS m/z: 308.1 [M+1].

Workup

temperaturethe reaction mixture was cooled to 25° C.
customevaporated onto silica gel
custompurified by flash column chromatography
washeluting with 2M NH3 in MeOH:CH2Cl2 (0:1→3:97)

Sources & evidence

ORD record: ord-83b0fef311a14e18ab6a74188e843285
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700593B2

Reaction notes

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