Potassium Carbonate → HCID 50899432, compound

HRID 2390770Notes

Reaction equation

HRID 2390770 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=3)=[N:10][N:11]([CH2:13][C:14]#[N:15])[CH:12]=2)[CH:5]=[C:4]([NH:25][CH2:26][C@@H:27]([OH:29])[CH3:28])[N: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+]>C(#N)C.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[OH:29][C@@H:27]([CH3:28])[CH2:26][NH:25][C:4]1[N:3]=[C:2]([C:32]2[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=2)[N:7]=[C:6]([C:8]2[C:9]([C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([O:23][CH3:24])[CH:17]=3)=[N:10][N:11]([CH2:13][C:14]#[N:15])[CH:12]=2)[CH:5]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 50899431HCID 50899431, compound

Product 1

HCID 50899432HCID 50899432, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

In a two-necked round-bottom flask, [4-[2-chloro-6-(2(S)-hydroxy-propylamino)-pyrimidin-4-yl]-3-(3-methoxy-5-methylphenyl)pyrazol-1-yl]acetonitrile (370 mg, 0.9 mmol), 3-pyridine boronic acid (143.27 mg, 1.17 mmol), bis(triphenylphosphine)palladium (II) dichloride (18.88 mg, 0.027 mmol), and potassium carbonate (75.98 mg, 0.72 mmol) were dissolved in a mixture of acetonitrile and water (10 mL, 1:1, v/v) through which nitrogen gas was then flowed for 10 min and heated at 75° C. for 3 hours. After completion of the Suzuki coupling reaction, the reaction mixture was dissolved in water and extracted with dichloromethane. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and distilled under vacuum. The purification of the concentrate by chromatography produced the title compound (274 mg, 67.1%).

Workup

  1. customAfter completion of the Suzuki coupling reaction
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under vacuum
  6. customThe purification of the
  7. concentrationconcentrate by chromatography

Sources & evidence

ORD record
ord-8e800d6390274e269b9439ecbbf63926
Source dataset
uspto-grants-2012_09
Patent number
US08273880B2

Reaction notes

Loading…