1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine → methyl 1-(3-chlorophenyl)-6-(furan-2-yl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1054308Notes

Reaction equation

HRID 1054308 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([NH2:13])=[CH:11][C:10]([CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](=O)[CH2:21][C:22](=O)[C:23]([O:25][CH3:26])=[O:24]>CC(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[N:13]=[C:20]([C:16]4[O:15][CH:19]=[CH:18][CH:17]=4)[CH:21]=[C:22]([C:23]([O:25][CH3:26])=[O:24])[C:11]=3[C:10]([CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 18106301-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amineHCID 2771615Methyl 4-(furan-2-yl)-2,4-dioxobutanoate

Product 1

HCID 25528590methyl 1-(3-chlorophenyl)-6-(furan-2-yl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(see, e.g., Volochnyuk, D. M., et al., J Comb Chem 2010, 12, 510-7). A solution of 22 (306 mg, 1.47 mmol) and 20 (295 mg, 1.50 mmol) in glacial AcOH (10 mL) was heated to reflux for 3 h. When the reaction mixture was cooled down to room temperature, yellow precipitates formed which were filtered and washed with H2O. Filtercake was placed in a vacuum oven to give the title compound (470 mg, 87%) as a yellow solid. 1H NMR (500 MHz, CDCl3) δ 8.48 (s, 1H), 8.29 (d, J=9.1 Hz, 1H), 8.06 (s, 1H), 7.62 (s, 1H), 7.43 (t, J=8.1 Hz, 1H), 7.28-7.23 (m, 2H), 6.63-6.59 (m, 1H), 4.06 (s, 3H), 2.75 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 165.53, 152.95, 151.82, 148.42, 144.43, 143.32, 140.31, 134.59, 133.91, 129.93, 125.41, 120.77, 118.52, 113.87, 112.57, 112.24, 110.94, 52.73, 16.21.

Workup

  1. temperatureto reflux for 3 h
  2. customyellow precipitates
  3. customformed which
  4. filtrationwere filtered
  5. washwashed with H2O

Sources & evidence

ORD record
ord-807b20a4a175416db1c21edc7391806b
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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