Sodium Carbonate → benzoic acid N'-[2-(5-fluoro-2'-nitro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250909

Reaction equation

HRID 2250909 reaction equation
Br[C:2]1[CH:24]=[C:23]([F: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+].[N+:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O)([O-:34])=[O:33]>COCCOC>[F:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][CH2:5][C:6]([N:8]([CH:18]([CH3:20])[CH3:19])[NH:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:7])=[C:2]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N+:32]([O-:34])=[O:33])[CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2773548(2-Nitrophenyl)boronic acidHCID 58689907benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

Product 1

HCID 11546901benzoic acid N'-[2-(5-fluoro-2'-nitro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazideYield 21.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (50 mg, 0.122 mmol) in DME (3 ml)/2M Na2CO3 (0.215 ml, 0.427 mmol) was treated with 2-nitrophenylboronic acid (31 mg, 0.183 mmol) and Pd[PPh3]4 (28 mg, 0.0244 mmol) for 12 hours at 90° C. 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 purified first on a silica gel column with 30% ethyl acetate/hexanes and then by RP HPLC to afford the product as a white solid (12 mg, 21%). MS m/e 452.18 (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 purified first on a silica gel column with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e6c87778d27f4407afa49e2391ab51fa
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Linked notes

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