Benzene → Ethyl 1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476120

Reaction equation

HRID 476120 reaction equation
O=[C:2]([CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:17][CH:18]([N:20]1[C:24]([NH2:25])=[CH:23][CH:22]=[N:21]1)[CH3:19].C1C=CC=CC=1>C(O)(=O)C>[CH3:17][CH:18]([N:20]1[C:24]2[N:25]=[C:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:23]=2[CH:22]=[N:21]1)[CH3:19]

Participants

5

Reactant 3

HCID 241BenzeneHCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl esterHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 46538388Ethyl 1-(1-methylethyl)-6-phenyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared in the same manner as described for intermediate 61 using ethyl 2,4-dioxo-4-phenylbutanoate (5 g, 22.7 mmol), 1-(1-methylethyl)-1H-pyrazol-5-amine (2.84 g, 22.7 mmol), benzene (70 mL), and acetic Acid (44 mL) The crude product was purified by silica gel chromatography (eluent: 0 to 100% EtOAc/hexanes) to give 6.72 g (95%) as a pale yellow solid. LCMS E-S (M+H)=310.5. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.17-8.28 (m, 3H), 7.49-7.64 (m, 3H), 5.38 (quin, J=6.69 Hz, 1H), 4.49 (q, J=7.07 Hz, 2H), 1.57 (d, J=6.57 Hz, 6H), 1.44 (t, 3H).

Workup

  1. customwas purified by silica gel chromatography (eluent: 0 to 100% EtOAc/hexanes)
  2. customto give 6.72 g (95%) as a pale yellow solid

Sources & evidence

ORD record
ord-de00594635b0481c88e99866406d9e72
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Linked notes

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