Dichloromethane → HCID 67337256, compound

HRID 451446Notes

Reaction equation

Br[C:2]1[C:3]2[N:4]([N:11]=[C:12]([NH2:14])[N:13]=2)[CH:5]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[CH:7]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>O1CCOCC1.O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3]3[N:4]([N:11]=[C:12]([NH2:14])[N:13]=3)[CH:5]=[C:6]([CH:8]3[CH2:10][CH2:9]3)[CH:7]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 8-bromo-6-cyclopropyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (300 mg, 1.29 mmol) and 4-chlorophenyl boronic acid (463 mg, 2.96 mmol) in dioxane (15 mL) was added an aqueous solution of Na2CO3 (2 M, 2 mL) and degassed with argon for 5 minutes. PdCl2 (dppf)2.CH2Cl2 (30.34 mg, 0.04 mmol) was added and stirred at 80° C. for 90 minutes. The reaction mixture was cooled to room temperature and water (20 mL) was added. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over sodium sulfate, the solvent was evaporated and the residue purified by silica gel chromatography using ethyl acetate/hexane as eluent. The title compound was obtained as an off white solid (252 mg, 75%).

Workup

customdegassed with argon for 5 minutes
temperatureThe reaction mixture was cooled to room temperature
extractionThe aqueous phase was extracted with ethyl acetate
dry with materialthe combined organic phases were dried over sodium sulfate
customthe solvent was evaporated
customthe residue purified by silica gel chromatography

Sources & evidence

ORD record: ord-96e1b2c8600b40b2a836113ac3595347
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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