3,4-Dichlorobenzeneboronic acid → HCID 118341151, compound

HRID 925807Notes

Reaction equation

HRID 925807 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.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][C:24]=1[Cl:25]>>[Cl:18][C:19]1[CH:20]=[C:21]([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:22]=[CH:23][C:24]=1[Cl:25]

Participants

3

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 118341151HCID 118341151, compound

Procedure

The title compound, off-white solid (80 mg, 90%), MS (ISP) m/z=356.3 [(M+H)+], mp 330.5° 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 3,4-dichloro-phenylboronic acid (62.0 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-53a8945dab614fbb9495cb55c370818f
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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