Triethylamine → HCID 57941529, compound

HRID 1437979Notes

Reaction equation

HRID 1437979 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:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.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:16]1[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339863-Fluorophenylboronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941529HCID 57941529, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-methyl-hydrazinecarboxylic acid tert-butyl ester (Intermediate 1; 570 mg, 4.1 mmol), 3-fluorophenylboronic acid (Aldrich; 673 mg, 4.6 mmol), copper(II) acetate (750 mg, 4.1 mmol) and triethylamine (1.4 mL, 10.0 mmol) in 1,2-dichloroethane (20 mL) was heated in an oil bath at 60° C. for 1.5 h. 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 10-20% ethyl acetate/hexanes, to give N′-(3-fluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (386 mg, 39%) as a pale yellow oil.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 10-20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a994e8a1b819496197165fb9245b1e7d
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

Loading…