Dimethylformamide → HCID 59437464, compound

HRID 2382884Notes

Reaction equation

HRID 2382884 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([NH:11][C:12](=[O:19])[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)[CH:7]=1.[F-].[Cs+].[CH3:22][N:23]([CH:25]=O)[CH3:24]>O>[C:12]([NH:11][C:9]1[N:10]=[C:5]2[CH:4]=[CH:3][C:2]([C:16]3[CH:17]=[CH:18][C:13]([C:12]([NH:11][CH2:9][CH2:25][N:23]([CH3:22])[CH3:24])=[O:19])=[CH:14][CH:15]=3)=[CH:7][N:6]2[N:8]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 25953Cesium fluorideHCID 25212517N-(6-bromo[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide

Product 1

HCID 59437464HCID 59437464, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a reaction vessel containing N-(6-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-benzamide ((B5), 95 mg, 0.3 mmol, 1 mol eq.), N-(2-dimethylamino-ethyl)-4-boronic acid-benzamide (85 mg, 0.36 mmol, 1.2 mol eq.) and cesium fluoride (135 mg, 0.9 mmol, 3 mol eq.) in DMF (0.75 mL) and H2O (0.5 mL) was added bis-triphenylphosphine palladium dichloride (0.009 mmol, 3 mol %) in DMF (0.25 mL). The vessel was purged with nitrogen, capped and heated at 95° C. for approximately 18 hours. The reaction mixture was cooled to room temperature, filtered and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (30.4 mg, 24%). HPLC, Rt: 1.74 min (purity: 99%). LC/MS M+(ESI): 429.3, M−(ESI) 427.4.

Workup

  1. customThe vessel was purged with nitrogen
  2. customcapped
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. dissolutionthe residue dissolved in DMSO (1.5 mL)
  6. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-4f8c6afbc65b414abfe0ec46388febd5
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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