Triethylamine → HCID 57941387, compound

HRID 1438060Notes

Reaction equation

HRID 1438060 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]=[CH:14][C:15]([C:21]([F:24])([F:23])[F:22])=[C:16](B(O)O)[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:17]=[C:12]([F:11])[CH:13]=[CH:14][C:15]=1[C:21]([F:22])([F:23])[F:24])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 37482801-Boc-1-methylhydrazine2×HCID 24901780[5-Fluoro-2-(trifluoromethyl)phenyl]boronic acid

Product 1

HCID 57941387HCID 57941387, compoundYield 45.9%

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; 400 mg, 2.74 mmol), 5-fluoro-2-(trifluoromethyl)phenylboronic acid (Cuschem, Inc., Yonkers, N.Y.; 512 mg, 2.46 mmol), copper(II) acetate (497 mg, 2.74 mmol) and triethylamine (380 μL, 2.7 mmol) in 1,2-dichloroethane (18 mL) was heated in an oil bath at 50° C. for 2 h. The mixture was allowed to cool, and it was then adsorbed onto silica gel and purified by chromatography using an ISCO 40 g column, eluting with 10% ethyl acetate/hexanes, to give N′-(5-fluoro-2-trifluoromethyl-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (348 mg, 41%) as a colorless oil that solidified.

Workup

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

Sources & evidence

ORD record
ord-0396e4fcb7234bf5adde7aa0c677e47d
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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