Potassium Carbonate → HCID 86721285, compound

HRID 1750443Notes

Reaction equation

HRID 1750443 reaction equation
Br[C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[O:18])[N:15]=1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[C:7]([N:6]1[C:2]([C:31]2[CH:32]=[CH:33][C:28]([Cl:27])=[CH:29][CH:30]=2)=[C:3]([C:11]2[S:12][CH:13]=[C:14]([CH2:16][C:17]([NH:19][CH2:20][CH:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[O:18])[N:15]=2)[CH:4]=[N:5]1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 86721244HCID 86721244, compound

Product 1

HCID 86721285HCID 86721285, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixed solution of 2-[2-(5-bromo-1-tert-butyl-1H-pyrazol-4-yl)thiazol-4-yl]-N-[(tetrahydro-2H-pyran-4-yl)methyl]acetamide (44.1 mg, 100 μmol), 4-chlorophenylboronic acid (15.6 mg, 100 μmol), potassium carbonate (27.6 mg, 200 μmol) and bis[di-tert-butyl(4-dimethylaminophenyl)phosphine]dichloropalladium(II) (7.08 mg, 10.00 μmol) in 1,2-dimethoxyethane (0.5 mL) and water (0.5 mL) was stirred at 150° C. for 30 min under ultrasonic irradiation. To the reaction solution was added water (1 mL), the mixture was extracted with ethyl acetate (2 mL), and the organic layer was concentrated. The residue was purified by preparative HPLC to give the title compound (17.9 mg, 0.038 mmol, 38%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2 mL)
  2. concentrationthe organic layer was concentrated
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b8ae8ab665d448fe86dc933a3d010d19
Source dataset
uspto-grants-2015_10
Patent number
US09156837B2

Reaction notes

Loading…