Sodium Carbonate → HCID 11510255, compound

HRID 2250919Notes

Reaction equation

HRID 2250919 reaction equation
Br[C:2]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7].C([O-])([O-])=O.[Na+].[Na+].[CH2:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O)[CH3:33]>COCCOC>[CH2:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[C:2]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH3:33]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 41008622-Ethylphenylboronic Acid (contains varying amounts of Anhydride)HCID 58689902HCID 58689902, compound

Product 1

HCID 11510255HCID 11510255, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[2-(2-bromo-4-methyl-phenoxy)-acetyl]-N′-isopropyl-hydrazide (100 mg, 0.247 mmol) in DME (3 ml)/2M Na2CO3 (0.435 ml, 0.8645 mmol) was treated with 2-ethylphenylboronic acid (74 mg, 0.493 mmol), Pd[PPh3]4 (29 mg, 0.0247 mmol in a microwave oven at 150° C. for 10 min. The reaction mixture was partitioned between water and ethyl acetate. 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 20-40% ethyl acetate/hexanes gradient to afford the product as a white solid (77 mg, 72%). MS m/e 431.34 (M+H+)

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  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 20-40% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-820d4c16eec14e72a5fe666a75ec6bb0
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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