Technology Process of 4-fluoro-N-((3R,4S)-3-hydroxy-6-(piperazin-1-yl)chroman-4-yl)benzamide
There total 10 articles about 4-fluoro-N-((3R,4S)-3-hydroxy-6-(piperazin-1-yl)chroman-4-yl)benzamide 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:
- Guidance literature:
-
(3R,4S)-4-amino-6-bromochroman-3-ol; 4-fluorobenzoyl chloride;
With
sodium hydrogencarbonate;
In
tetrahydrofuran; water;
at 0 - 25 ℃;
for 3.5h;
Large scale;
piperazine;
With
bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate;
In
tetrahydrofuran; dimethyl sulfoxide; toluene;
at 70 ℃;
for 4h;
Inert atmosphere;
Large scale;
DOI:10.1021/ml500283g
- Guidance literature:
-
piperazine; N-[(3R,4S)-6-bromo-3-hydroxy-chroman-4-yl]-4-fluoro-benzamide;
With
sodium t-butanolate;
bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate;
In
dimethyl sulfoxide; toluene;
at 70 ℃;
for 4h;
Inert atmosphere;
With
hydrogenchloride;
In
water; dimethyl sulfoxide; ethyl acetate; toluene;
for 0.5h;
pH=6 - 7;
With
sodium hydroxide;
In
water;
pH=11 - 12;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: toluene-4-sulfonic acid / toluene / 3.83 h / 50 °C / Reflux; Industry scale
2.1: N-Bromosuccinimide; water / dimethyl sulfoxide / 1.5 h / 0 - 5 °C
3.1: ammonium hydroxide / isopropyl alcohol; water / 15 h / 20 °C
4.1: D-(+)-camphoric acid / acetonitrile; water / 0.17 h / 70 - 75 °C
4.2: 50 °C
5.1: sodium hydrogencarbonate / water; tetrahydrofuran / 2.25 h / 17 °C / Industry scale
6.1: sodium t-butanolate / bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate / toluene; dimethyl sulfoxide / 4 h / 70 °C / Inert atmosphere
6.2: 0.5 h / pH 6 - 7
6.3: pH 11 - 12
With
ammonium hydroxide; N-Bromosuccinimide; D-(+)-camphoric acid; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; sodium t-butanolate;
bis(η3-allyl-μ-chloropalladium(II)); tri tert-butylphosphoniumtetrafluoroborate;
In
tetrahydrofuran; water; dimethyl sulfoxide; isopropyl alcohol; toluene; acetonitrile;
