Benzene → Ethyl 1,6-bis(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 476098

Reaction equation

HRID 476098 reaction equation
[CH3:1][C:2]([CH3:14])([CH3:13])[C:3](=O)[CH2:4][C:5](=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C1C=CC=CC=1.[CH3:21][C:22]([N:25]1[C:29]([NH2:30])=[CH:28][C:27]([CH3:31])=[N:26]1)([CH3:24])[CH3:23]>C(O)(=O)C>[CH3:24][C:22]([N:25]1[C:29]2[N:30]=[C:3]([C:2]([CH3:14])([CH3:13])[CH3:1])[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:28]=2[C:27]([CH3:31])=[N:26]1)([CH3:21])[CH3:23]

Participants

5

Reactant 3

HCID 241BenzeneHCID 83403Ethyl 5,5-dimethyl-2,4-dioxohexanoateHCID 7372001-tert-Butyl-3-methyl-1H-pyrazol-5-amine

Product 1

HCID 68081092Ethyl 1,6-bis(1,1-dimethylethyl)-3-methyl-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 5,5-dimethyl-2,4-dioxohexanoate (392 mg, 1.958 mmol), benzene (10 mL), 1-(1,1-dimethylethyl)-3-methyl-1H-pyrazol-5-amine (300 mg, 1.958 mmol), and acetic acid (2 mL). The crude product was purified by column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 530 mg (85%) of product. LCMS E-S (M+H)=318.3. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.43-1.52 (m, 12H), 1.84 (s, 9H), 2.67 (s, 3H), 4.50 (q, J=7.07 Hz, 2H), 7.59 (s, 1H).

Workup

  1. customThe crude product was purified by column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-040262c2b0be4256a7c5b9a3d0da0ef9
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Linked notes

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