4-Chlorophenylboronic acid → 6-(4-Chloro-phenyl)-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925653Notes

Reaction equation

HRID 925653 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]([F:16])[CH:3]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][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]([F:16])[CH:3]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 900359066-(4-Chloro-phenyl)-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, light grey solid (75 mg, 95%), MS (ISP) m/z=315.1 [(M+H)+], mp 322° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 1) (70.8 mg, 0.25 mmol) and commercially available 4-chloro-phenylboronic acid (50.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-9528b46f94204dfeb5ce09baa09c1086
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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