Acetonitrile → tert-butyl 1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

HRID 1774988노트

반응식

HRID 1774988 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([N:17]4[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:19][CH2:18]4)[CH:14]=[N:15][CH:16]=3)=[N:9][N:8]([CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[C:5]2=[CH:6][N:7]=1.[N:37]1[CH:42]=[CH:41][CH:40]=[C:39](B(O)O)[CH:38]=1.C(#N)C.C([O-])(=O)C.[K+]>O.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[CH:12]=[C:13]([N:17]5[CH2:22][CH2:21][CH:20]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:19][CH2:18]5)[CH:14]=[N:15][CH:16]=4)=[N:9][N:8]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][O:32]4)[C:5]3=[CH:6][N:7]=2)[CH:38]=1

참가 물질

8

반응물 4

HCID 6342AcetonitrileHCID 517044Potassium AcetateHCID 27343783-Pyridinylboronic acidHCID 86676686tert-butyl 1-(5-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

생성물 1

HCID 71253755tert-butyl 1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 962Water용매2회HCID 10340Sodium Carbonate용매

실험 절차

To a mixture of tert-butyl 1-(5-(5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate (45.0 mg, 0.0807 mmol), 3-Pyridylboronic acid (29.8 mg, 0.242 mmol) and 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (9.888 mg, 0.01211 mmol) in Acetonitrile (1.01 mL, 19.4 mmol) was added 1.0 M of Potassium acetate in Water (0.121 mL) and 1.0 M of Sodium carbonate in Water (0.121 mL). The reaction mixture was irradiated in microwave at 125° C. for 20 min. The reaction was filtered thru celite. The filtrate was washed H2O and brine. The organic layer was dried with Na2SO4, filtered, and concentrated to give tert-butyl 1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate.

후처리

  1. customThe reaction mixture was irradiated in microwave at 125° C. for 20 min
  2. filtrationThe reaction was filtered thru celite
  3. washThe filtrate was washed H2O and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a3591398fd72450a914d05331ff47c7e
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260425B2

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