Hydrochloric Acid → HCID 178490902, compound

HRID 387555Notes

Reaction equation

HRID 387555 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:21]=[CH:20][C:8]([CH2:9][N:10]2[C:14]3[N:15]=[CH:16][CH:17]=[C:18]([OH:19])[C:13]=3[CH:12]=[N:11]2)=[CH:7][CH:6]=1.C(=O)(O)[O-].[Na+].Cl>C(O)C>[Br:1][C:17]1[CH:16]=[N:15][C:14]2[N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:21][CH:20]=3)[N:11]=[CH:12][C:13]=2[C:18]=1[OH:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 178490904HCID 178490904, compound

Product 1

HCID 178490902HCID 178490902, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Bromine (1.39 mL, 27.03 mmol) was added drop wise over 5 minutes to a solution of 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (6.00 g, 23.50 mmol, prepared as described in WO 2007/103308) in absolute ethanol (60 mL) at 0° C. The reaction was stirred at 0° C. for 1 hour. 5% Sodium bicarbonate solution (100 mL) was then added, and the mixture was concentrated to give a slurry. The pH was next adjusted with 1N HCl to a pH of 4. The resulting solid was collected by filtration and dried. This solid was then suspended in ether (50 mL), stirred for 10 minutes, collected by filtration and dried to give 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (6.8 g, 87%). MS ESI (+) m/z 334 detected. 1H NMR (400 Hz, DMSO-d6) δ 12.68 (s, 1H), 8.34 (s, 1H), 8.13 (s, 1H), 7.18 (d, J=8.8 Hz, 2H), 6.87 (d, J=8.4 Hz, 2H), 5.47 (s, 2H), 3.70 (s, 3H).

Workup

  1. concentrationthe mixture was concentrated
  2. customto give a slurry
  3. filtrationThe resulting solid was collected by filtration
  4. customdried
  5. stirringstirred for 10 minutes
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-0645fd6a5fba40d3a9eb5cd81a0b88b3
Source dataset
uspto-grants-2013_02
Patent number
US08372842B2

Reaction notes

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