(4-Methoxyphenyl)boronic acid → 8-Fluoro-6-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925649Notes

Reaction equation

HRID 925649 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.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[F:16][C:4]1[CH:3]=[C:2]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[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]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 900365878-Fluoro-6-(4-methoxy-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, white solid (33 mg, 43%), MS (ISP) m/z=311.3 [(M+H)+], mp 274.5° 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 4-methoxy-phenylboronic acid (49.4 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-d6f840fc126847a382a63491d9f59b54
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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