Water → HCID 71254231, compound

HRID 1775113Notes

Reaction equation

HRID 1775113 reaction equation
Br[C:2]1[C:3]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[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.[CH3:44]B(O)O.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>[CH3:44][C:2]1[C:3]([N:31]2[CH2:35][CH2:34][C@@H:33]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[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]([CH3:28])([CH3:30])[CH3:29])[N:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 139377Methylboronic AcidHCID 517044Potassium AcetateHCID 71253861HCID 71253861, compound

Product 1

HCID 71254231HCID 71254231, compoundYield 39%

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 (R)-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)pyrrolidin-3-ylcarbamate (124.5 mg, 0.1867 mmol), Methyl boronic acid (111.76 mg, 1.867 mmol), 1,1′-Bis(diphenylphosphino)ferrocenepalladium (II) chloride (15.2 mg, 0.01876 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 (R)-tert-butyl 1-(3-methyl-6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)pyrrolidin-3-ylcarbamate (43.8 mg, 39%).

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-3fbf273ceb004e4dbbe00bf1df652852
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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