3,5-Dichlorophenylboronic acid → HCID 90035811, compound

HRID 925908Notes

Reaction equation

HRID 925908 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]=[C:24]([Cl:26])[CH:25]=1>>[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]=[C:24]([Cl:26])[CH:25]=1

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035811HCID 90035811, compound

Procedure

The title compound, light grey solid (58 mg, 62%), MS (ISN) m/z=368.4 [(M−H)+], mp 347° 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 3,5-dichloro-phenylboronic acid (62.0 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-5324273b28df440988b39b277b792b3a
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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