Triethylamine → HCID 57941323, compound

HRID 1437995Notes

Reaction equation

HRID 1437995 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[C:17]([F:18])=[CH:16][CH:15]=[CH:14][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:16]1[CH:15]=[CH:14][CH:13]=[C:12]([F:11])[C:17]=1[F:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734333(2,3-Difluorophenyl)boronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941323HCID 57941323, compoundYield 52%

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; 500 mg, 3.4 mmol), 2,3-difluorophenylboronic acid (Aldrich; 529 mg, 3.35 mmol), copper(II) acetate (621 mg, 3.4 mmol) and triethylamine (480 μL, 3.4 mmol) in 1,2-dichloroethane (4 mL) was heated in an oil bath at 50° C. for 3 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 20-40% ethyl acetate/hexanes, to give N′-(2,3-difluoro-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (450 mg, 39%) as a colorless oil.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 20-40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-07ebcacacc89460e9cd5c5702e7ea948
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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