Ethanol → 3-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid

HRID 643672Notes

Reaction equation

HRID 643672 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:9][N:10]=[C:4]2[CH:3]=1.B([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:24]([OH:26])=[O:25])(O)O.C(=O)([O-])[O-].[Na+].[Na+].CCO>COCCOC.CO.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.O>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[N:5]2[CH:6]=[CH:7][C:2]([C:21]3[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:24]([OH:26])=[O:25])=[CH:3][C:4]2=[N:10][N:9]=1

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 189801423-Borono-4-methylbenzoic acidHCID 498716717-Chloro-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 592613633-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 7-chloro-3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridine (1.77 g, 6.7 mmol), 3-borono-4-methylbenzoic acid (1.57 g, 8.7 mmol), Pd(PPh3)2Cl2 (0.329 g, 0.46 mmol, Strem), and sodium carbonate (2.13 g, 20 mmol, JT Baker) in DME:EtOH:H2O=7:2:3 (8 ml) was heated to 80° C. for 8 h. The mixture was cooled to room temperature, diluted with MeOH and filtered through Celite. The filtrate was concentrated to yield the title compound as a brown solid. MS (ESI, pos. ion) m/z: 364.0 (M+1).

Workup

  1. filtrationfiltered through Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-751a1a3676684f27a7aded26bdfbce68
Source dataset
uspto-grants-2010_04
Patent number
US07700593B2

Reaction notes

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