69088-96-6

Usage

Uses

Used in Chemical Synthesis Industry:
4-(3-Aminophenyl)-2-methyl-3-butyn-2-ol is used as a reactant in cross-coupling reactions for the synthesis of various aromatic and heteroaromatic compounds. Its presence in these reactions facilitates the formation of new carbon-carbon bonds, which is crucial for the creation of complex organic molecules and pharmaceutical intermediates.
In the context of cross-coupling reactions, 4-(3-AMINOPHENYL)-2-METHYL-3-BUTYN-2-OL serves as a key intermediate, enabling the synthesis of a wide range of organic compounds with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science. The ability of 4-(3-Aminophenyl)-2-methyl-3-butyn-2-ol to participate in these reactions highlights its importance in modern organic chemistry and its contribution to the development of new and innovative chemical products.

InChI:InChI=1/C11H13NO/c1-11(2,13)7-6-9-4-3-5-10(12)8-9/h3-5,8,13H,12H2,1-2H3

Upstream product

• 115-19-5 2-methyl-but-3-yn-2-ol 
• 626-01-7 3-Iodoaniline 
• 591-19-5 m-Bromoaniline 
• 33432-52-9 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol 
• 50624-25-4 4-hydroxy-4-methyl-2-pentynoic acid 
• 108-42-9 3-chloro-aniline 
• 585-79-5 m-nitrobromobenzene 

Downstream Products

• 54060-30-9 3-acetylenephenylamine 
• 31661-59-3 3-(4-(3-aminophenyl)buta-1,3-diynyl)benzeneamine 
• 299912-59-7 3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride 
• 1611477-69-0 3-(3-aminophenyl)-5,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxaborol-2(5H)-ol 
• 67-64-1 acetone 
• 248594-19-6 N-(3-ethynylphenyl)-6,7-bis(2-methoxyethoxy)-4-quinazolinamine, methanesulfonic acid salt 
• 183319-69-9 erlotinib hydrochloride 

Relevant academic research and scientific papers

Fast heck-cassar-sonogashira (hcs) reactions in green solvents

The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.

New method for the preparation of erlotinib

The present invention refers to an alternative method for the preparation of Erlotinib through a new chemical reaction for the preparation of the 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol key intermediate of formula (IV) according to the following scheme.

METHOD FOR THE PREPARATION OF ERLOTINIB

An alternative method for the preparation of Erlotinib through a new chemical reaction for the preparation of the 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol key intermediate of formula (IV) according to the following scheme.

Process for preparing 3-aminophenylacetylenes

A process for preparing a 3-aminophenylacetylene compound of formula (5), including: a) reacting a 3-haloaniline compound of formula (1) with an acetylene compound of formula (2) in the presence of a palladium compound, a copper compound, and an amine compound of formula (3) to form an aniline compound of formula (4); b) precipitating the aniline compound of formula (4) in the form of a crystal, and isolating it by solid/liquid separation; and c) reacting the aniline compound of formula (4) with a base to obtain 3-aminophenylacetylene.

N-benzylidene aminophenylacetylene carbinols

This invention provides a process for preparing aminoarylacetylenes comprising reacting a N-arylmethylidene aminoarylhalide with a terminal acetylene in the presence of a base and a catalyst system comprising a palladium catalyst and a cuprous salt to pro

Process for the industrial preparation of aminoacetylenes

A process for the preparation of 3-aminophenylacetylene derivatives of formula: STR1 wherein R1 is as defined in the disclosure STR2 wherein Y is as defined in the disclosure wherein R is as defined in the disclosure.

A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y)

An efficient, high-yielding synthetic procedure for the preparation of the novel neuronal acetylcholinegated ion channel agonist (S)-(-)-5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine maleate [(S)-2, SIB-1508Y] is described. The key steps in the process include the lithium bis(trimethylsilyl)amide-mediated acylation of N-vinylpyrrolidinone with ethyl 5-bromonicotinate, a high-yielding sodium borohydride reduction of imine 5, and a new heteroaryl-alkyne cross-coupling protocol for the introduction of the ethyne moiety in (S)-2. The preparation of enantiomerically pure (S)-2 was accomplished via a combination of enantioselective reduction of imine 5 and crystallization of enantiomerically enriched 5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine (7) as the dibenzoyl-L-tartaric acid salt.

Synthesis of Some Substituted Dimethyl and Diethyl 4-(Phenylethynyl)-2,6-pyridinedicarboxylates

Substituted dimethyl and diethyl 4-(phenylethynyl)-2,6-pyridinedicarboxylates were prepared by coupling reactions between dialkyl 4-halo-2,6-pyridinedicarboxylates and terminal arylacetylenes in the presence of an organopalladium catalyst and copper(I) iodide in a suitable solvent system.The terminal acetylenes needed in this work were synthesized from the corresponding aryl halides using either (trimethylsilyl)acetylene or 2-methyl-3-butyn-2-ol followed by deprotection of the triple bond, depending on the nature of the compound in question.

Selective hydrogenation of nitro groups on nitroaromatic acetylenes using an unsupported cobalt polysulfide catalyst

Aromatic nitroacetylene compounds wherein both the nitro and acetylene groups are directly connected to aromatic ring carbon atoms are hydrogenated at high conversion levels to selectively reduce the nitro function using an unsupported cobalt polysulfide catalyst. Of particular interest is the preparation of aminophenylacetylenes from nitrophenylacetylene.