Sodium Carbonate Monohydrate → 3-(3-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-cyclopropyl-4-methylbenzamide

HRID 643678Notes

Reaction equation

HRID 643678 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]2[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])=[N:10][N:11]=[C:4]2[CH:3]=1.[CH:19]1([NH:22][C:23](=[O:40])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26](B3OC(C)(C)C(C)(C)O3)[CH:25]=2)[CH2:21][CH2:20]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>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:9]1[N:5]2[C:6]([CH3:8])=[CH:7][C:2]([C:26]3[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=3[CH3:30])[C:23]([NH:22][CH:19]3[CH2:20][CH2:21]3)=[O:40])=[CH:3][C:4]2=[N:11][N:10]=1

Participants

7

Reactant 3

HCID 2735133Sodium Carbonate MonohydrateHCID 21914577N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 592613657-Chloro-3-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 592613643-(3-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-N-cyclopropyl-4-methylbenzamideYield 239.9%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
140 °C

Procedure

In a microwave tube was placed 7-chloro-3-(2-chlorophenyl)-5-methyl-[1,2,4]triazolo[4,3-a]pyridine (0.061 g, 0.22 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.086 g, 0.29 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.013 g, 0.018 mmol) and sodium carbonate monohydrate (0.16 g, 1.3 mmol) in 1 mL of DME and 0.4 mL of water. The mixture was heated in the microwave at 140° C. for 15 min. Water was then added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to give 220 mg of a brown oil. The crude material was purified by silica gel chromatography (0-5% MeOH in DCM) to afford the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 417.2 (M+1).

Workup

  1. customIn a microwave tube was placed
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c5dc353620a46ffbca8c6c464d38cb3
Source dataset
uspto-grants-2010_04
Patent number
US07700593B2

Reaction notes

Loading…