3-Pyridinylboronic acid → HCID 90036690, compound

HRID 925913Notes

Reaction equation

HRID 925913 reaction equation
Br[C:2]1[C:10]2[N:9]3[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]3=[C:7]([CH3:17])[C:6]=2[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22](B(O)O)[CH:21]=1>>[CH3:17][C:7]1[C:6]2[CH:5]=[C:4]([C:18]#[N:19])[CH:3]=[C:2]([C:22]3[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=3)[C:10]=2[N:9]2[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:8]=12

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 90036394HCID 90036394, compound2×

Product 1

HCID 90036690HCID 90036690, compound

Procedure

The title compound, off-white solid (42 mg, 53%), MS (ISP) m/z=317.6 [(M+H)+], mp 260° C., was prepared in accordance with the general method of example 1 from 7-bromo-11-methyl-1-oxo-2,3,4,5-tetrahydro-[1,4]diazepino[1,2-a]indole-9-carbonitrile (intermediate 17) (79.5 mg, 0.25 mmol) and commercially available pyridin-3-ylboronic acid (39.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-b93681e48d3a446eac6d4c84dabfa119
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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