tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Base Information

• Chemical Name: tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate
• CAS No.: 155601-71-1
• Molecular Formula: C11H12FN3O2
• Molecular Weight: 237.234
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70427821
• Wikidata: Q82240531
• Mol file: 155601-71-1.mol

Synonyms:155601-71-1;tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate;tert-butyl 6-fluoro-2H-pyrazolo[3,4-b]pyridine-3-carboxylate;6-Fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid tert-butyl ester;tert-Butyl6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate;MFCD06797502;tert-Butyl 6-fluoro-1H-pyrazolo-[3,4-b]pyridine-3-carboxylate;3-Boc-6-fluoro-1H-pyrazolo[3,4-b]pyridine;1H-Pyrazolo[3,4-b]pyridine-3-carboxylic acid, 6-fluoro-, 1,1-dimethylethyl ester;3-(tert-Butoxycarbonyl)-6-fluoro-1H-pyrazolo[3,4-b]pyridine;C11H12FN3O2;SCHEMBL492450;DTXSID70427821;AKOS015904438;PS-6372;SB33906;SY250431;CS-0311096;FT-0756146;t-Butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Chemical Property of tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 165.5-168.5 °C
• Refractive Index: 1.585
• Boiling Point: 378 °C at 760 mmHg
• Flash Point: 182.4 °C
• PSA: 67.87000
• Density: 1.318 g/cm³
• LogP: 2.05230
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 237.09135480
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

tert-Butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Harmful:

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C1=C2C=CC(=NC2=NN1)F

Technology Process of tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate

There total 5 articles about tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

water (7732-18-5) + 2,6-Difluoropyridine-3-(α-oxo)acetic acid, t-butyl ester (155601-70-0) → tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (155601-71-1)

Guidance literature:

With hydrazine hydrate; Ti(O-IPr)4; In dichloromethane;

Reference yield:

t-butyl-2,6-difluoro-α-oxo-3-acetate hydrazone → tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (155601-71-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 0.333333h; Yield given;

DOI:10.1002/jhet.5570340314

Reference yield:

2,6-difluoro pyridine (1513-65-1) → tert-butyl 6-fluoro-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (155601-71-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium diisopropylamide*THF complex / 1.) cyclohexane, -65 deg C, 2.) THF, cyclohexane, -65 deg C, 30 min

2: titanium(IV) isopropoxide, hydraziner hydrate / CH₂Cl₂ / 1 h

3: NaH / tetrahydrofuran / 0.33 h

With titanium(IV) isopropylate; sodium hydride; hydrazine hydrate; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/jhet.5570340314

upstream raw materials:

2,6-difluoro pyridine

tert-butyl α-oxo-1H-imidazole-1-acetate

2,6-Difluoropyridine-3-(α-oxo)acetic acid, t-butyl ester

water

Downstream raw materials:

6-Fluoro-1H-pyrazolo[3,4-b]pyridine-3-carbonitrile

3-chloro-5-{[5-chloro-1-({1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methyl)-1H-indazol-4-yl]oxy}benzonitrile

3-(chloromethyl)-N,1-bis(methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-6-amine

{1-(4-methoxybenzyl)-6-[(4-methoxybenzyl)amino]-1H-pyrazolo[3,4-b]pyridin-3-yl}methanol

Refernces

• 1、 -. "6-PIPERAZINYL-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBOXYLIC ACIDS, ESTERS, AMIDES AND RELATED COMPOUNDS". . . Retrieved 2008/06/13.