Water → HCID 57949551, compound

HRID 2427773Notes

Reaction equation

HRID 2427773 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([Cl:11])[CH:10]=1)[C:7](=[O:12])[N:6]([CH2:13][C:14]#[C:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5]2.CC1(C)C(C)(C)OB([C:30]2[CH:31]=[N:32][N:33]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH:34]=2)O1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.Cl[Pd]Cl>[NH3:6].[Cl:11][C:9]1[CH:10]=[C:2]([C:30]2[CH:31]=[N:32][N:33]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[CH:34]=2)[CH:3]=[C:4]2[C:8]=1[C:7](=[O:12])[N:6]([CH2:13][C:14]#[C:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5]2

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 179991861-(Pyridin-2-ylmethyl)-1H-pyrazole-4-boronic acid, pinacol esterHCID 57949310HCID 57949310, compound

Product 2

HCID 222AmmoniaHCID 57949551HCID 57949551, compoundYield 128%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-7-chloro-2-(3-phenylprop-2-ynyl)-2,3-dihydroisoindol-1-one (60 mg, 0.167 mmol) in DMF (4 mL) was added 2-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)pyrazol-1-ylmethyl]pyridine (61.71 mg, 0.216 mmol), PdCl2 (13.57 mg, 0.017 mmol), and K2CO3 (70 mg, 0.5 mmol). The mixture was heated at 110° C. overnight, then poured into water and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. Column chromatography (4% (2M NH3 in MeOH)/CH2Cl2) provided the title compound (46.9 mg, 64%). 1H NMR (300 MHz, CDCl3): δ (ppm) 8.61 (d, 1H), 7.90 (dd, 1H), 7.45 (m, 4H), 7.32 (m, 5H), 7.18 (d, 1H), 5.49 (s, 2H), 4.66 (s, 2H), 4.53 (s, 2H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-76df91c1542f4651b6c164dea0e56658
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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