4-Chloro-3-(trifluoromethyl)benzeneboronic acid → HCID 73335413, compound

HRID 925819Notes

Reaction equation

HRID 925819 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][C:20]=1[C:28]([F:31])([F:30])[F:29]>>[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][C:20]=1[C:28]([F:29])([F:30])[F:31]

Participants

3

Reactant 2

HCID 27826714-Chloro-3-(trifluoromethyl)benzeneboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 73335413HCID 73335413, compound

Procedure

The title compound, white solid (63 mg, 65%), MS (ISN) m/z=388.4 [(M−H)+], mp 347° 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-3-trifluoromethyl-phenylboronic acid (72.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-34ce61da90fe45d4b32b40569c831254
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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