Potassium Carbonate → HCID 178428483, compound

HRID 1952352Notes

Reaction equation

HRID 1952352 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7]([OH:13])=[N:8][CH:9]=[CH:10][C:11]=1[CH3:12].Br[CH2:19][C:20]1[C:28]2[C:23](=[N:24][CH:25]=[CH:26][CH:27]=2)[N:22](C(OC(C)(C)C)=O)[N:21]=1.C(=O)([O-])[O-].[K+].[K+]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:14]=[C:15]([Cl:17])[CH:16]=1)[O:5][C:6]1[C:7](=[O:13])[N:8]([CH2:19][C:20]2[C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[NH:22][N:21]=2)[CH:9]=[CH:10][C:11]=1[CH3:12]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 10828872tert-Butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylateHCID 178428607HCID 178428607, compound

Product 1

HCID 178428483HCID 178428483, compound

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(3-bromo-5-chlorophenoxy)-4-methylpyridin-2-ol (11-5; 75 mg, 0.238 mmol) and tert-butyl 3-(bromomethyl)-1H-pyrazolo[3,4-b]pyridine-1-carboxylate (74.4 mg, 0.238 mmol) was added potassium carbonate (33 mg, 0.238 mmol) and the resulting mixture was stirred at 25° C. for 18 hours. After this time, the mixture was filtered and then purified on Gilson LC using a Luna column (10μ, C18, 250×21.2 cm) eluting with 5-95% ACN/water with 0.1% TFA). The desired fractions were concentrated to dryness and the resulting solid was dissolved in trifluoroacetic acid (2 mL) This solution was concentrated on the rotary evaporator to give the title compound. LRMS (M+1)=446.7

Workup

  1. filtrationAfter this time, the mixture was filtered
  2. custompurified on Gilson LC
  3. washeluting with 5-95% ACN/water with 0.1% TFA)
  4. concentrationThe desired fractions were concentrated to dryness
  5. dissolutionthe resulting solid was dissolved in trifluoroacetic acid (2 mL) This solution
  6. concentrationwas concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-cfd99d5972e6464b8d87549b6e3aff8c
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

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