Water → 6-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

HRID 2279138Notes

Reaction equation

HRID 2279138 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=[C:10](Br)[CH:11]=1)=[O:5])[CH3:2].[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.O.C(OCC)(=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:15]([CH3:16])=[N:14][N:13]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[C:8]=2[N:9]=[C:10]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH2:25][O:24][CH3:23])=[CH:28][CH:29]=2)[CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27625284-(Methoxymethoxy)phenylboronic acidHCID 866803196-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester

Product 1

HCID 900137956-(4-Methoxymethoxy-phenyl)-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl esterYield 107.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a degassed mixture of 1.68 g 6-bromo-3-methyl-1-(tetrahydro-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid ethyl ester, 1.00 g 4-(methoxymethoxy)-phenylboronic acid and 0.70 g potassium carbonate in DME/water (v/v=2/1, 24 mL) at r.t. and under Ar-atmosphere 70 mg palladium(0) bis(tri-tert-butylphosphine) was added and the mixture was stirred at 85° C. for 1 h. To the mixture water and ethyl acetate were added, the phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. 2.08 g (100%) of the title compound were obtained.

Workup

  1. additionunder Ar-atmosphere 70 mg palladium(0) bis(tri-tert-butylphosphine) was added
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5604f7e767dd46a0910abfac81f3d725
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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