3-Cyanophenylboronic acid → HCID 90035845, compound

HRID 925809Notes

Reaction equation

HRID 925809 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.[C:18]([C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1)#[N:19]>>[C:18]([C:20]1[CH:25]=[C:24]([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:23]=[CH:22][CH:21]=1)#[N:19]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90035845HCID 90035845, compound

Procedure

The title compound, white solid (69 mg, 88%), MS (ISP) m/z=313.4 [(M+H)+], mp 253° 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 3-cyanophenylboronic acid (47.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-a573252ba260408aade5a11ef7471b7e
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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