3-Pyridinylboronic acid → HCID 90035928, compound

HRID 925897Notes

Reaction equation

HRID 925897 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=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1>>[CH3:16][C:7]1[C:6]2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=[C:2]([C:21]3[CH:20]=[N:19][CH:24]=[CH:23][CH:22]=3)[C:10]=2[N:9]2[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]=12

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035928HCID 90035928, compound

Procedure

The title compound, white solid (60 mg, 79%), MS (ISN) m/z=301.4 [(M−H)+], mp 273° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available pyridin-3-ylboronic acid (39.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-2079c6ce19ba48409fd13e298d31399c
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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