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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 886580
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HRID 886580 반응식
[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
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참가 물질

9

반응물 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

생성물 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

시약·촉매·용매 4

HCID 53485975CID 53485975촉매HCID 1140Toluene용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-8e48f853e6184fc3b3b2b93c00122b72
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08242280B2

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