Triethylamine → HCID 57941428, compound

HRID 1437989Notes

Reaction equation

HRID 1437989 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:10])[NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O)([CH3:13])[CH3:12].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]=[CH:18][CH:19]=[C:14]([CH:11]([CH3:13])[CH3:12])[CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27734772-Isopropylbenzeneboronic acidHCID 37482801-Boc-1-methylhydrazine2×

Product 1

HCID 57941428HCID 57941428, compoundYield 26.7%

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; 300 mg, 2.05 mmol), 2-isopropylphenylboronic acid (Lancaster; 330 mg, 2.01 mmol), copper(II) acetate (373 mg, 2.05 mmol) and triethylamine (287 μL, 2.05 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 5% ethyl acetate/hexanes, to give N′-(3-isopropyl-phenyl)-N-methyl-hydrazinecarboxylic acid tert-butyl ester (142 mg, 26%) as an oil.

Workup

  1. temperatureto cool
  2. custompurified by chromatography
  3. washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e433656b7e614ddea6526dcc5d168e8b
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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