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

HRID 1724140Notes

Reaction equation

HRID 1724140 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][CH:35]=[CH:34][C:33]=1B(O)O>COCCOC>[CH:22]([N:12]([C:10](=[O:11])[CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[CH3:31])[NH:13][C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 57560116Benzoic acid N'-[3-(2-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide

Product 1

HCID 57560127Benzoic acid N'-isopropyl-N'-[3-(2'-methyl-biphenyl-2-yl)-propionyl]-hydrazideYield 18%

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-methyl-phenylboronic acid (27 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 (9 mg, 18%). LC-MS m/e 401.29 (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-df3402615e694f22ba98e2ffa99df2d0
Source dataset
uspto-grants-2009_02
Patent number
US07485752B2

Reaction notes

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