Trifluoroacetic acid → 3,4-Diphenyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-6-one

HRID 1594028Notes

Reaction equation

C([N:5]1[C:9]2[NH:10][C:11](=[O:20])[CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]=2[C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:6]1)(C)(C)C.C(O)(C(F)(F)F)=O>>[C:21]1([C:7]2[NH:6][N:5]=[C:9]3[C:8]=2[C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:12][C:11](=[O:20])[NH:10]3)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 136338636HCID 136338636, compound

Product 1

HCID 1354779133,4-Diphenyl-2,7-dihydro-pyrazolo[3,4-b]pyridin-6-oneYield 20%

Conditions

Temperature: 70 °C

Procedure

To 1-tert-butyl-3,4-diphenyl-1,7-dihydro-pyrazolo[3,4-b]pyridin-6-one (1.0 g, 3.1 mmol) was added neat TFA (15 mL) and the resulting solution was heated to 70° C. After 18 hr, the reaction was concentrated under reduced pressure to remove TFA. The resulting tan solid was diluted with EtOAc and washed with an aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered through a fritted funnel, and concentrated under reduced pressure. Purification of this material was accomplished by recrystallization from MeOH to give the title compound (0.17 g, 20% yield) as a colorless solid. LRMS m/z (APCl) 288 (M+1); 500 MHz 1H NMR (DMSO-D6) δ 7.29-6.92 (m, 10H), 5.90 (bs, 1H).

Workup

concentrationthe reaction was concentrated under reduced pressure
customto remove TFA
additionThe resulting tan solid was diluted with EtOAc
washwashed with an aqueous solution of NaHCO3
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered through a fritted funnel
concentrationconcentrated under reduced pressure
customPurification of this material
customwas accomplished by recrystallization from MeOH

Sources & evidence

ORD record: ord-34178ac2dc1d40d399477fe6982135c8
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300943B2

Reaction notes

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