Sodium Carbonate → Benzoic acid N'-[3-(2',5'-dimethyl-biphenyl-2-yl)-propionyl]-N'-isopropyl-hydrazide

HRID 1724131Notes

Reaction equation

HRID 1724131 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11].C([O-])([O-])=O.[Na+].[Na+].[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1B(O)O>COCCOC>[CH3:31][C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][C:33]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([N:12]([CH:22]([CH3:24])[CH3:23])[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734347(2,5-Dimethylphenyl)boronic acidHCID 57560116Benzoic acid N'-[3-(2-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide

Product 1

HCID 11954396Benzoic acid N'-[3-(2',5'-dimethyl-biphenyl-2-yl)-propionyl]-N'-isopropyl-hydrazideYield 26%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[3-(2-bromo-phenyl)-propionyl]-N′-isopropyl-hydrazide (50 mg, 0.13 mmol) in DME (4 ml)/2M Na2CO3 (225 μL, 0.45 mmol) was treated with 2,5-dimethyl-phenylboronic acid (29 mg, 0.19 mmol) and Pd[PPh3]4 (15 mg, 0.013 mmol) for 18 hours at 90° C. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient to afford the product as a solid (14 mg, 26%). LC-MS m/e 415.36 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was absorbed on silica
  7. custompurified on a silica gel column with a 20-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-6be04f7da4f8472f9798ef64cf6d64fb
Source dataset
uspto-grants-2009_02
Patent number
US07485752B2

Reaction notes

Loading…