2-Chloropyridine-5-boronic acid → HCID 90036036, compound

HRID 925841Notes

Reaction equation

HRID 925841 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]3=[CH:7][C:6]=2[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=1.[Cl:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[N:24]=[CH:23][C:22]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 38450342-Chloropyridine-5-boronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90036036HCID 90036036, compound

Procedure

The title compound, off-white solid (62 mg, 77%), MS (ISN) m/z=323.5 [(M+H)+], mp 300.5° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 6-chloro-pyridin-3-ylboronic acid (51.1 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-dd186feae9244651a122c197f7ad3ed7
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

Loading…