Sodium Carbonate → {3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-methyl-pyridin-2-yl)-methanol

HRID 886580Notes

Reaction equation

HRID 886580 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH:16]=2)[N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:10]=1.Br[C:36]1[CH:37]=[C:38]([CH:42]([C:44]2[C:49]([CH3:50])=[CH:48][CH:47]=[CH:46][N:45]=2)[OH:43])[CH:39]=[CH:40][CH:41]=1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+]>C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe].ClCCl.C1(C)C=CC=CC=1.C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:40]3[CH:39]=[C:38]([CH:42]([C:44]4[C:49]([CH3:50])=[CH:48][CH:47]=[CH:46][N:45]=4)[OH:43])[CH:37]=[CH:36][CH:41]=3)[CH:16]=2)[N:11]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:33])[CH3:34])[N:10]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 59825051(3-Bromo-phenyl)-(3-methyl-pyridin-2-yl)-methanolHCID 598360923-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxy-methyl)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 59825045{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-methyl-pyridin-2-yl)-methanol

Reagents, catalysts & solvents 4

HCID 53485975CID 53485975CatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

415 mg (0.87 mmol) of 3-(2-methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridine, 40 mg (49 μmol) of dichloro[1,1′-bis(diphenyl-phoshino)ferrocene]palladium(II) dichloromethane adduct and 240 mg (0.86 mmol) of (3-bromo-phenyl)-(3-methyl-pyridin-2-yl)-methanol were place in a microwave vial. 6 mL of acetonitrile, 2 mL of toluene and 6 mL of a saturated aqueous solution of sodium carbonate were added. The vial was sealed and irradiated in a Personal Chemistry® Optimizer to 145° C. for 30 main. The resulting mixture was distributed between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous layer was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulfate and evaporated. The resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford a yellow oil. MS: m/z 553.0 (M+H+).

Workup

  1. customThe vial was sealed
  2. customirradiated in a Personal Chemistry® Optimizer to 145° C. for 30 main
  3. extractionThe aqueous layer was extracted twice with dichloromethane
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes
  7. customto afford a yellow oil

Sources & evidence

ORD record
ord-8e48f853e6184fc3b3b2b93c00122b72
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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