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Diisopropylethylamine → cyclohexanecarboxylic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250888
Notes
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Reaction equation

HRID 2250888 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH:14]([NH:17][NH:18][C:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>CN(C=O)C>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([N:17]([CH:14]([CH3:16])[CH3:15])[NH:18][C:19]([CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)=[O:20])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3028732-(2-Bromo-4-fluorophenoxy)acetic acidHCID 2733179PyBroPHCID 58689912cyclohexane carboxylic acid N'-isopropyl-hydrazide

Product 1

HCID 58689911cyclohexanecarboxylic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazideYield 75%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-bromo-4-fluoro-phenoxy)-acetic acid (249 mg, 1.0 mmol) and cyclohexane carboxylic acid N′-isopropyl-hydrazide (221 mg, 1.2 mmol) in DMF (10 ml) was treated with diisopropylethyl amine (0.44 mL, 2.5 mmol) and bromotripyrrolidinophosphonium hexafluorophosphate (PyBroP, 700 mg, 1.5 mmol) at room temperature overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate. The organic layer was successively washed with saturated 1N NaOH and brine, then dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50% ethyl acetate/hexanes gradient to afford the product as a white solid (310 mg, 75%).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and ethyl acetate
  2. washThe organic layer was successively washed with saturated 1N NaOH and 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 30-50% ethyl acetate/hexanes gradient

Sources & evidence

ORD record
ord-d7acf529473b408781834070f3debe80
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07317125B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes