Sodium Carbonate Monohydrate → N-cyclopropyl-3-(3-(isopropylamino)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzamide

HRID 643681Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:9][N:10]=[C:4]2[CH:3]=1.[CH:15]1([NH:18][C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=2)[CH2:17][CH2:16]1.O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.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>[CH:15]1([NH:18][C:19](=[O:36])[C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([C:2]3[CH:7]=[CH:6][N:5]4[C:8]([NH:11][CH:12]([CH3:14])[CH3:13])=[N:9][N:10]=[C:4]4[CH:3]=3)[CH:21]=2)[CH2:16][CH2:17]1

Participants

Conditions

Temperature: 150 °C

Procedure

In a microwave tube was placed 7-bromo-N-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine (0.105 g, 0.41 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.16 g, 0.54 mmol), trans-dichlorobis(triphenyl-phosphine)palladium (II) (0.024 g, 0.034 mmol) and sodium carbonate monohydrate (0.29 g, 2.3 mmol) in 2.8 mL of DME and 1.1 mL of water. The mixture was heated in the microwave at 150° C. for 15 min. Water was then added and the mixture was extracted with DCM (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 203 mg of a black solid. The crude material was purified by silica gel chromatography (0-5% MeOH in DCM) to afford the title compound as a pale yellow solid. MS (ESI, pos. ion) m/z: 350.4 (M+1).

Workup

customIn a microwave tube was placed
extractionthe mixture was extracted with DCM (3×)
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-6fb0b5282edf4ef1ba781bd18ca9595c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700593B2

Reaction notes

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