Hydrochloric Acid → 3-Bromo-1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522510Notes

Reaction equation

[Br:1][C:2]1[C:10]2[C:9]([C:11]([O:13]CC)=[O:12])=[CH:8][C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:6][C:5]=2[N:4]([CH:22]([CH3:24])[CH3:23])[N:3]=1.[OH-].[Na+].Cl>C1COCC1.C(O)C.O>[Br:1][C:2]1[C:10]2[C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[N:6][C:5]=2[N:4]([CH:22]([CH3:24])[CH3:23])[N:3]=1

Participants

Conditions

Temperature: 55 °C

Procedure

Ethyl 3-bromo-1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (112 mg, 0.288 mmol) was suspended in THF (0.5 mL) and ethanol (1.5 mL), followed by addition of 3N NaOH (150 μl, 0.433 mmol). The reaction mixture was stirred at 55° C. for 3 hours, and then allowed to cool to room temperature. The reaction mixture was diluted with water (1.5 mL), cooled in an ice bath, and acidified with 1N HCl in a dropwise manner. The mixture was extracted with EtOAc. The organic layer was separated and concentrated in vacuo to afford a solid that dried on the high vacuum 3 hours. The product was collected as a pale yellow solid (93.6 mg, 90%). LCMS E-S (M+H)=360.0/362.2. 1H NMR (400 MHz, MeOD) δ8.22 (dd, J=1.52, 8.08 Hz, 2H), 8.05 (s, 1H), 7.48-7.59 (m, 3H), 5.47 (quip, J=6.76 Hz, 1H), 1.63 (d, J=6.82 Hz, 6H)

Workup

temperatureto cool to room temperature
temperaturecooled in an ice bath
extractionThe mixture was extracted with EtOAc
customThe organic layer was separated
concentrationconcentrated in vacuo
customto afford a solid
customthat dried on the high vacuum 3 hours
customThe product was collected as a pale yellow solid (93.6 mg, 90%)

Sources & evidence

ORD record: ord-baa8ffda3789425e8c3cce48ea99f7a2
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073924B2

Reaction notes

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