3,4-Dichlorobenzeneboronic acid → HCID 90036389, compound

HRID 925875Notes

Reaction equation

HRID 925875 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=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=1.[Cl:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[Cl:26]>>[Cl:19][C:20]1[CH:21]=[C:22]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

3

Reactant 2

HCID 27343303,4-Dichlorobenzeneboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90036389HCID 90036389, compound

Procedure

The title compound, grey solid (46 mg, 50%), MS (ISP) m/z=370.3 [(M+H)+], mp 245° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available 3,4-dichloro-phenylboronic acid (62.0 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-50e25f11080f4ad7a4149540eb786b92
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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