4-Chlorophenylboronic acid → HCID 90036370, compound

HRID 925695Notes

Reaction equation

HRID 925695 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:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([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:21][CH:20]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 90036370HCID 90036370, compound

Procedure

The title compound, off-white solid (68 mg, 85%), MS (ISP) m/z=322.4 [(M+H)+], mp 316.5° 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 4-chloro-phenylboronic acid (50.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-eda50484560846e9afca592a64db8ffe
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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