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

HRID 925652Notes

Reaction equation

HRID 925652 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.[F:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[F:24]>>[F:17][C:18]1[CH:19]=[C:20]([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:21]=[CH:22][C:23]=1[F:24]

Participants

3

Reactant 2

HCID 27343373,4-Difluorobenzeneboronic acidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 900362796-(3,4-Difluoro-phenyl)-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, light grey solid (72 mg, 91%), MS (ISP) m/z=317.1 [(M+H)+], mp 289.5° 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 3,4-difluoro-phenylboronic acid (51.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-68606ebe740a4329b6d876812d1547a0
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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