Tolylboronic acid → 8-Fluoro-6-p-tolyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925654Notes

Reaction equation

HRID 925654 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.B(O)(O)[C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1>>[F:16][C:4]1[CH:3]=[C:2]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=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 79799Tolylboronic acidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 1183411828-Fluoro-6-p-tolyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, light grey solid (70 mg, 95%), MS (ISP) m/z=295.2 [(M+H)+], mp 271.5° 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 p-tolylboronic acid (44.2 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-eec7513a270e4f0db15e33d418fa92f7
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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