Phenol → HCID 67335999, compound

HRID 451472Notes

Reaction equation

Br[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CC=CC=1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I.O>[O:18]([C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine (see example 66b, 500 mg, 2.35 mmol), phenol (442 mg, 4.69 mmol), copper(I) iodide (44.7 mg, 235 μmol), picolinic acid (57.8 mg, 469 μmol) and potassium phosphate tribasic (1.49 g, 7.04 mmol) in DMSO (10 mL) was heated to 120° C. After 12 hours further phenol (442 mg, 4.69 mmol), copper(I) iodide (44.7 mg, 235 μmol), picolinic acid (57.8 mg, 469 μmol) and potassium phosphate tribasic (1.49 g, 7.04 mmol) were added and stirred at 120° C. for another 18 hours. Water was added to the reaction mixture and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and the solvent was evaporated. The crude material was purified by prep. HPLC. The title compound was obtained as off-white solid (200 mg, 38%).

Workup

extractionthe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic phases were dried over sodium sulfate
customthe solvent was evaporated
customThe crude material was purified by prep

Sources & evidence

ORD record: ord-fde1a0e5d536499d93c48142a1fe3646
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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