(Pyrimidin-5-yl)boronic acid → HCID 73335894, compound

HRID 925840Notes

Reaction equation

HRID 925840 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]=[C:22](B(O)O)[CH:21]=[N:20][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:22]4[CH:23]=[N:18][CH:19]=[N:20][CH:21]=4)[C:10]=3[N:9]2[CH2:11][CH2:12][NH:13]1

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 73335894HCID 73335894, compound

Procedure

The title compound, off-white solid (16 mg, 22%), MS (ISN) m/z=290.5 [(M+H)+], mp 323.5° 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 pyrimidin-5-ylboronic acid (40.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-bdfa09e843b044189668226d60515442
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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