5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

Base Information

Chemical Name:5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide
CAS No.:912454-36-5
Molecular Formula:C₁₉H₂₁BrN₂O₃
Molecular Weight:405.291
Hs Code.:

Synonyms:5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

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Chemical Property of 5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

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Technology Process of 5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

There total 5 articles about 5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide 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: 49.0%

: 912454-75-2
6-benzyloxy-5-bromo-3-pyridinecarboxylic acid

: 13374-31-7
(1R,2R)-trans-2-aminocyclohexanol hydrochloride

: 912454-36-5
5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

Guidance literature:: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1021/jm4010708

Reference yield:

: 41668-13-7
5-bromo-6-hydroxy-3-pyridinecarboxylic acid

: 912454-36-5
5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

2: potassium hydroxide / dimethyl sulfoxide / 0.13 h / 100 °C / Inert atmosphere; Microwave irradiation

3: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 4 h / 20 °C / Inert atmosphere

With quinoline; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; trichlorophosphate; In N,N-dimethyl acetamide; dimethyl sulfoxide;
DOI:10.1021/jm4010708

Reference yield:

: 5006-66-6
6-hydroxy-3-pyridinecarboxylic acid

: 912454-36-5
5-bromo-N-[(1R,2R)-2-hydroxycyclohexyl]-6-(phenylmethoxy)-3-pyridine carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1: acetic acid; bromine / 18.75 h / 45 - 50 °C / Inert atmosphere

2: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

3: potassium hydroxide / dimethyl sulfoxide / 0.13 h / 100 °C / Inert atmosphere; Microwave irradiation

4: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl acetamide / 4 h / 20 °C / Inert atmosphere

With quinoline; bromine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; acetic acid; N-ethyl-N,N-diisopropylamine; potassium hydroxide; trichlorophosphate; In N,N-dimethyl acetamide; dimethyl sulfoxide;
DOI:10.1021/jm4010708