144657-68-1

Basic information

• Product Name: tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate
• Synonyms: tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate;1-Boc-3-(ChloroMethyl)-1H-pyrrolo[2,3-b]pyridine;3-b]pyridine-1-carboxylate;tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2
• CAS NO: 144657-68-1
• Molecular Formula: C₁₃H₁₅ClN₂O₂
• Molecular Weight: 267
• Mol File: 144657-68-1.mol

Chemical Properties

• Boiling Point: 389.9°C at 760 mmHg
• Flash Point: 189.6°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 2.75E-06mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate(144657-68-1)
• EPA Substance Registry System: tert-butyl 3-(chloroMethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate(144657-68-1)

Safety Data

• Hazardous Substances Data: 144657-68-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H15ClN2O2/c1-13(2,3)18-12(17)16-8-9(7-14)10-5-4-6-15-11(10)16/h4-6,8H,7H2,1-3H3

Upstream product

• 144657-65-8 1-tert-butyloxycarbonyl-3-(N-dimethylaminomethyl)-7-azaindole 
• 144657-66-9 tert-butyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 5654-92-2 7-azagramine 
• 4649-09-6 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde 
• 271-63-6 7-Azaindole 
• 144657-67-0 tert-butyl 3-(hydroxymethyl)-1 H-pyrrolo[2,3-b]pyridine-1-carboxylate 

Downstream Products

• 134235-82-8 (-)-(R)-7-azatryptophan 
• 1268390-81-3 1-(2-methoxyl-5-chlorophenyl)-3-{1-[1-(t-butyloxycarbonyl)-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl]-1H-indol-4-yl}urea 
• 1029052-26-3 3-[6-(4-chloro-benzylamino)-pyridazin-3-ylmethyl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Asymmetric Synthesis of N-Fmoc-(S)-7-aza-tryptophan via Alkylation of Chiral Nucleophilic Glycine Equivalent

Ni(II)-complexes, derived from glycine Schiff bases with chiral tridentate ligands, have been used as powerful tools for the synthesis of structurally diverse tailor-made amino acids. In this manuscript, asymmetric alkylation reaction between chiral nucleophilic glycine derived Ni-complex and 3-(chloromethyl)-1H-pyrrolo[2,3-b]pyridine has been developed under convenient conditions, which affords the corresponding alkylated Ni-complex in 74 % yield and excellent diastereoselectivity (only one isomer). This reaction features convenient conditions and completely controlled diastereoselectivity, which provides a highly valuable approach for asymmetric synthesis of 7-aza-tryptophan.

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5,6-BICYCLIC HETEROARYL-CONTAINING UREA COMPOUNDS AS KINASE INHIBITORS

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The synthesis of (-)-(R)-7-azatryptophan (2) from commercially available 7-azaindole (4) is described.The key step involved the diastereoselective alkylation of tert-butyl acetate (3) with 1-(tert-butyloxycarbonyl-3-(iodomethyl)-7-azaindole (14).The alkylation, conducted at -100 deg C in a THF/HMPA solvent using potassium hexamethyldisilazide as the base, afforded 7 in a greater than 98 percent diastereomeric excess.Hydrolysis and deprotecting gave (-)-(R)-7-azatryptophan.