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 1774988ノート

反応式

HRID 1774988 の反応式
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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 10340Sodium Carbonate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a3591398fd72450a914d05331ff47c7e
出典データセット
uspto-grants-2016_02
特許番号
US09260425B2

反応ノート

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