Water → HCID 86676703, compound

HRID 1775110Notes

Reaction equation

HRID 1775110 reaction equation
Br[C:2]1[C:3]([N:31]2[CH2:36][CH2:35][CH2:34][C@H:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:32]2)=[N:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[N:10]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[N:9]=2)=[CH:6][CH:7]=1.[CH3:45][C:46]1(C)C(C)(C)OB(C=C)O1.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].C(#N)C>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:5]4[N:4]=[C:3]([N:31]5[CH2:36][CH2:35][CH2:34][C@H:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:43])[CH3:41])[CH2:32]5)[C:2]([CH:45]=[CH2:46])=[CH:7][CH:6]=4)=[N:9][N:10]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:28])([CH3:29])[CH3:30])[C:11]3=[CH:12][N:13]=2)[CH:18]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 517044Potassium AcetateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71253806HCID 71253806, compound

Product 1

HCID 86676703HCID 86676703, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
150 °C

Procedure

A microwave reaction vial was charged with (S)-tert-butyl 1-(3-bromo-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-3-ylcarbamate (128.3 mg, 0.189 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (320 uL, 1.9 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (15.4 mg, 0.0189 mmol), 1.00 M of Potassium acetate in Water (0.28 mL, 0.28 mmol), 1.00 M of Sodium carbonate in Water (0.28 mL, 0.28 mmol), and Acetonitrile (10 mL). The reaction mixture was heated under microwave at 150° C. for 5 minutes. The mixture was concentrated, and the residue was purified on silica eluted with 0 to 100% EtOAc in Heptane to afford (S)-tert-butyl 1-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-3-vinylpyridin-2-yl)piperidin-3-ylcarbamate (107 mg, 91%).

Workup

  1. customA microwave reaction
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified on silica
  4. washeluted with 0 to 100% EtOAc in Heptane

Sources & evidence

ORD record
ord-54d861187f044ea29ef4717fb0460d0d
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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