Potassium Hydroxide → 1-(3-Chlorophenyl)-6-(furan-2-yl)-3-methylpyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1054316Notes

Reaction equation

HRID 1054316 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[N:13]=[C:14]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=[C:16]([C:17]([O:19]C)=[O:18])[C:11]=3[C:10]([CH3:26])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>CC(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[N:13]=[C:14]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[CH:15]=[C:16]([C:17]([OH:19])=[O:18])[C:11]=3[C:10]([CH3:26])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 25528590methyl 1-(3-chlorophenyl)-6-(furan-2-yl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 41784861-(3-Chlorophenyl)-6-(furan-2-yl)-3-methylpyrazolo[3,4-b]pyridine-4-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

(see, e.g., Volochnyuk, D. M., et al., J Comb Chem 2010, 12, 510-7). A solution of ester 35 (108 mg, 0.29 mmol) and KOH (29 mg, 0.52 mmol) in iPrOH (6 mL) was refluxed for 1 h 30 min. Reaction mixture was diluted with H2O (10 mL) and washed with EtOAc (10 mL×2). Aqueous layer was acidified with 1N HCl and extracted with EtOAc (10 mL×2). Combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated under reduced pressure to give 1 (88 mg, 86%) as a bright yellow solid. 99% pure by HPLC. 1H NMR (400 MHz, DMSO-d6) δ 8.35 (s, 1H), 8.29 (d, J=8.5 Hz, 1H), 7.96 (s, 1H), 7.92 (s, 1H), 7.55 (t, J=8.1 Hz, 1H), 7.37-7.31 (m, 2H), 6.76-6.71 (m, 1H), 2.62 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 166.48, 152.40, 151.70, 148.29, 146.21, 143.65, 140.42, 136.54, 133.86, 131.32, 125.57, 119.83, 118.66, 113.69, 113.32, 112.21, 112.10, 16.20. ESI MS: m/z 354.0 (M+H)+.

Workup

  1. customReaction mixture
  2. washwashed with EtOAc (10 mL×2)
  3. extractionextracted with EtOAc (10 mL×2)
  4. washCombined organic extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b5aaf4275b29467fbbd0eb65ebffb41f
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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