1,2-Dimethoxyethane → 6-(4-Fluorophenyl)-2-methyl-5-(4-pyridyl)-4-[5-(3-pyridyl)thien-2-yl]pyrazolo[3,4-b]pyridine

HRID 42608Notes

Reaction equation

HRID 42608 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[N:10]=[C:9]3[NH:26][N:27]([CH3:29])[CH2:28][C:8]=23)=[CH:4][CH:3]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C([O-])([O-])=O.[K+].[K+].COCCOC>C(Cl)(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:11]2[C:12]([C:13]3[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=3)=[C:7]([C:5]3[S:6][C:2]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:3][CH:4]=3)[C:8]3[C:9](=[N:26][N:27]([CH3:29])[CH:28]=3)[N:10]=2)=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 670148754-(5-bromothien-2-yl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 670141676-(4-Fluorophenyl)-2-methyl-5-(4-pyridyl)-4-[5-(3-pyridyl)thien-2-yl]pyrazolo[3,4-b]pyridineYield 50%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-(5-bromothien-2-yl)-6-(4-fluorophenyl)-2-methyl-5-(4-pyridyl)-1H-pyrazolo[3,4-b]pyridine (0.10 g, 0.2 mmol, obtained in example 188), 3-pyridylboronic acid (0.04 g, 0.3 mmol), K2CO3 (0.06 g, 0.4 mmol), Pd(PPh3)4 (0.017 g, 0.01 mmol), 1,2-dimethoxyethane (1.31 mL) and water (0.04 mL) was heated at 80° C. under argon atmosphere overnight. It was allowed to cool and diluted with CHCl3 and water. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 35 mg of the desired compound (yield: 50%).

Workup

  1. temperatureto cool
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe crude product obtained
  5. customwas purified by chromatography on silica gel
  6. temperatureof increasing polarity as eluent

Sources & evidence

ORD record
ord-2772064505c84e01972480126ddcfd2f
Source dataset
uspto-grants-2013_09
Patent number
US08536194B2

Reaction notes

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