Potassium Carbonate → HCID 86651954, compound

HRID 1615267Notes

Reaction equation

HRID 1615267 reaction equation
Br[C:2]1[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.CN(C=O)C.O.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C>[N:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:10]=[C:9]([CH:11]=[O:12])[CH:8]=[C:7]3[C:3]=2[CH:4]=[N:5][N:6]3[CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2762745Pyridine-2-boronic acidHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 86651953HCID 86651953, compound

Product 1

HCID 86651954HCID 86651954, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (50 mg, 0.14 mmol) and pyridine boronic acid (20 mg, 0.16 mmol) in 10:1 DMF/water (1 mL) was added K2CO3 (36 mg, 0.26 mmol) and tetrakistriphenylphosphine palladium (7.5 mg, 0.007 mmol). The mixture was heated to 120° C. under microwave irradiation for 20 min. Ethyl acetate (20 mL) was added and the solution was washed with water (2×5 mL) and brine (5 mL), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (3:1 EtOAc/Hex) to give the title compound as a pale yellow solid (31 mg, 62%). MS ESI [M+H]+, calcd for [C19H23N3O2Si+H]+ 354.2; found m/z 354.2.

Workup

  1. washthe solution was washed with water (2×5 mL) and brine (5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (3:1 EtOAc/Hex)

Sources & evidence

ORD record
ord-12d64400b7244c10bf1712eefd617136
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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