Sodium Carbonate → 4-(2-methoxy-ethoxy)-benzoic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazide

HRID 2250931Notes

Reaction equation

HRID 2250931 reaction equation
Br[C:2]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:3]=1[O:4][CH2:5][C:6]([N:8]([CH:23]([CH3:25])[CH3:24])[NH:9][C:10](=[O:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=1)=[O:7].C([O-])([O-])=O.[Na+].[Na+].[F:37][C:38]([F:50])([F:49])[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O>COCCOC>[F:30][C:28]1[CH:27]=[CH:26][C:3]([O:4][CH2:5][C:6]([N:8]([CH:23]([CH3:25])[CH3:24])[NH:9][C:10](=[O:22])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[CH:13][CH:12]=2)=[O:7])=[C:2]([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=2[O:39][C:38]([F:37])([F:50])[F:49])[CH:29]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 586899194-(2-methoxy-ethoxy)-benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

Product 1

HCID 117210574-(2-methoxy-ethoxy)-benzoic acid N'-[2-(5-fluoro-2'-trifluoromethoxy-biphenyl-2-yloxy)-acetyl]-N'-isopropyl hydrazideYield 55%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-(2-methoxy-ethoxy)-benzoic acid N′-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N′-isopropyl-hydrazide (202 mg, 0.42 mmol) in DME (5 ml)/2M Na2CO3 (0.731 ml, 1.46 mmol) was with 2-trifluoromethoxyphenylboronic acid (129 mg, 0.63 mmol) and Pd[PPh3]4 (96.5 mg, 0.084 mmol) in a microwave oven at 150° C. for 10 min. 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 45-60% ethyl acetate/hexane gradient to afford the product as a solid (129 mg, 55%). MS m/e 565.55 (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 45-60% ethyl acetate/hexane gradient

Sources & evidence

ORD record
ord-08141d7cd694409d874fffc6faaa056a
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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