Ethanolamine → HCID 59264647, compound

HRID 645928Notes

Reaction equation

HRID 645928 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[S:13][C:14](Br)=[CH:15][CH:16]=2)[N:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:7]=1)=[O:5])[CH3:2].[CH3:26][C:27]([CH3:32])([CH3:31])[CH2:28][C:29]#C.C(N)CO.O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(OCC)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH3:11])=[C:9]([C:12]2[S:13][C:14]([C:29]#[C:28][C:27]([CH3:32])([CH3:31])[CH3:26])=[CH:15][CH:16]=2)[N:8]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[N:7]=1)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 5187601-Pentyne, 4,4-dimethyl-HCID 24808242HCID 24808242, compound

Product 1

HCID 59264647HCID 59264647, compoundYield 80%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 5-(5-bromo-thiophen-2-yl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (500 mg, 1.09 mmol), PdCl2(PPh3)2 (23 mg, 0.03 mmol), and CuI (4 mg, 0.01 mmol) in THF (10 mL) was added 4,4-dimethylpent-1-yne (176 mg, 1.30 mmol) and 0.5 M aqueous solution of 2-ethanolamine (3 mL). The resulting mixture was heated at 60° C. for 6 h. After cooled to room temperature, the reaction mixture was poured into water and diethyl ether (H2O/ether=1:1 (v/v), 20 mL). The aqueous layer was extracted with diethyl ether and the combined organic layers were concentrated to give a crude oil, which was purified by flash column chromatography with n-hexane/ethyl acetate (5:1) to afford the desired product (402 mg, 80%) as a light solid.

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. concentrationthe combined organic layers were concentrated
  4. customto give a crude oil, which
  5. customwas purified by flash column chromatography with n-hexane/ethyl acetate (5:1)

Sources & evidence

ORD record
ord-1578de0028d142f9b15232a9571485af
Source dataset
uspto-grants-2010_04
Patent number
US07705024B2

Reaction notes

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