3-Pyridinylboronic acid → HCID 73335615, compound

HRID 925844Notes

Reaction equation

HRID 925844 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.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH:19]=1>>[O:15]=[C:14]1[C:8]2=[CH:7][C:6]3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=[C:2]([C:20]4[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=4)[C:10]=3[N:9]2[CH2:11][CH2:12][NH:13]1

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 73335615HCID 73335615, compound

Procedure

The title compound, off-white solid (50 mg, 69%), MS (ISN) m/z=289.4 [(M+H)+], mp 272.5° 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 pyridin-3-ylboronic acid (39.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-df3e1083afbc4272a1176b414bc0c0cb
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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