Sodium Carbonate → 1-(1-Methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 476108Notes

Reaction equation

HRID 476108 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([O:22]CC)=[O:21])[C:11]3[CH:16]=[N:15][N:14]([CH:17]([CH3:19])[CH3:18])[C:12]=3[N:13]=2)=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:33]2[CH:34]=[N:35][NH:36][CH:37]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:19][CH:17]([N:14]1[C:12]2[N:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:33]4[CH:34]=[N:35][NH:36][CH:37]=4)=[CH:3][CH:4]=3)[CH:9]=[C:10]([C:20]([OH:22])=[O:21])[C:11]=2[CH:16]=[N:15]1)[CH3:18]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67124343Ethyl 6-(4-bromophenyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 671241631-(1-Methylethyl)-6-[4-(1H-pyrazol-4-yl)phenyl]-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acidYield 35%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 5-mL microwave vial were added ethyl 6-(4-bromophenyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (80 mg, 0.206 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (56.0 mg, 0.288 mmol), 1,4-dioxane (2 mL) and sodium carbonate (0.206 mL, 0.412 mmol), and the mixture was degassed with nitrogen for 10 min. Next added PdP(Ph3)4 (19.05 mg, 0.016 mmol) and the vial was sealed. The reaction mixture was irradiated (microwave) at 120° C. overnight. The reaction mixture was filtered and concentrated in vacuo. The residue was purified using reverse-phase HPLC to give 25 mg (35%) of product. LCMS E-S (M+H)=348.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (d, J=6.8 Hz, 6H), 5.38 (quin, J=6.6 Hz, 1H), 7.81 (d, J=8.3 Hz, 2H), 8.14-8.30 (m, 4H), 8.36 (s, 1H).

Workup

  1. customthe mixture was degassed with nitrogen for 10 min
  2. customthe vial was sealed
  3. customThe reaction mixture was irradiated (microwave) at 120° C. overnight
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-95f3f29c09224c2eb00e803df36d8fff
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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