(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

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Chemical Name:(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester
CAS No.:1605313-20-9
Molecular Formula:C₂₁H₂₅FN₂O₃
Molecular Weight:372.44
Hs Code.:

Synonyms:(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

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Chemical Property of (±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

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Technology Process of (±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

There total 3 articles about (±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester 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: 93.0%

: 1403901-49-4
6-bromo-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

: 459-57-4
4-fluorobenzaldehyde

: 1605313-20-9
(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: 6-bromo-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

4-fluorobenzaldehyde; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/acs.jmedchem.8b00900

Reference yield:

: 1403901-48-3
(5-bromo-2-iodo-pyridin-3-yl)-(2-methyl-allyl)-amine

: 1605313-20-9
(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine; palladium diacetate; sodium formate; tetrabutyl-ammonium chloride / water; dimethyl sulfoxide / 1 h / 100 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

2.2: 1.75 h

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: 0.5 h / -78 °C

With n-butyllithium; potassium tert-butylate; tetrabutyl-ammonium chloride; sodium formate; palladium diacetate; triethylamine; In tetrahydrofuran; hexane; water; dimethyl sulfoxide;

Reference yield:

: 1259512-11-2
6-bromo-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

: 1605313-20-9
(±)-6-[(4-fluoro-phenyl)-hydroxy-methyl]-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 1.75 h

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

With n-butyllithium; potassium tert-butylate; In tetrahydrofuran; hexane;