Triethylamine → HCID 57941356, compound

HRID 1438033Notes

Reaction equation

HRID 1438033 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1B(O)O.C(N(CC)CC)C>ClCCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]([CH3:10])[NH:9][C:13]1[C:12]([F:11])=[CH:17][CH:16]=[CH:15][C:14]=1[F:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343362,6-Difluorophenylboronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941356HCID 57941356, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 1.00 g, 6.8 mmol), 2,6-difluorophenylboronic acid (Aldrich; 1.07 g, 6.8 mmol), copper(II) acetate (1.24 g, 6.8 mmol) and triethylamine (960 μL, 6.8 mmol) in 1,2-dichloroethane (15 mL) was heated in an oil bath at 50° C. overnight. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 120 g column, eluting with 20-25% ethyl acetate/hexanes, to give N′-(2,6-difluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (167 mg, 9%) as a colorless oil.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 20-25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0b9154fd8d914f21a7e799904eae5773
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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