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

HRID 476107Notes

Reaction equation

HRID 476107 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][CH:3]=1.C1C=CC=CC=1.[CH3:24][CH:25]([N:27]1[C:31]([NH2:32])=[CH:30][CH:29]=[N:28]1)[CH3:26]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:30]3[CH:29]=[N:28][N:27]([CH:25]([CH3:26])[CH3:24])[C:31]=3[N:32]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 10903411-(propan-2-yl)-1H-pyrazol-5-amineHCID 11066474Ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate

Product 1

HCID 67124343Ethyl 6-(4-bromophenyl)-1-(1-methylethyl)-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 4-(4-bromophenyl)-2,4-dioxobutanoate (956 mg, 3.20 mmol), benzene (10 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (4 mL). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 1.1 g (89%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49-1.57 (t, J=67.2 Hz, 3H), 1.63-1.74 (d, J=6.8 Hz 6H), 4.56 (q, J=7.2 Hz, 2H), 5.46 (spt, J=6.7 Hz, 1H), 7.65-7.71 (m, 2H), 8.04-8.15 (m, 2H), 8.21 (s, 1H), 8.42 (s, 1H).

Workup

  1. customThe crude product was purified

Sources & evidence

ORD record
ord-9a3645af6cfb41d786532fc6286d4e98
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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