Sodium Carbonate → benzoic acid N'-[2-(2'-methoxy-biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

HRID 2250944Notes

Reaction equation

HRID 2250944 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S: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][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O>COCCOC>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S: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 27339582-Methoxyphenylboronic acidHCID 58689908benzoic acid N'-[2-(2-bromo-phenylsulfanyl)-acetyl]-N'-isopropyl-hydrazide

Product 1

HCID 11633465benzoic acid N'-[2-(2'-methoxy-biphenyl-2-ylsulfanyl)-acetyl]-N'-isopropyl-hydrazideYield 55.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[2-(2-bromo-phenylsulfanyl)-acetyl]-N′-isopropyl-hydrazide (100 mg, 0.246 mmol) in DME (5 ml)/2M Na2CO3 (0.43 ml, 0.86 mmoles) was treated with 2-methoxyphenylboronic acid (75 mg, 0.49 mmol) and Pd[PPh3]4 (28 mg, 0.025 mmol) for 12 hours at 90° C. The reaction mixture was partitioned between water and DCM. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was adsorbed on silica and purified on a silica gel column with a 20-50% ethyl acetate/hexane gradient to afford the product as a solid (59 mg, 54%). MS m/e 435.23 (M+H+)

Workup

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

Sources & evidence

ORD record
ord-78b302436c194088962eaaccf933fad1
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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