Phenylboronic Acid → 8-Fluoro-6-phenyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925644Notes

Reaction equation

HRID 925644 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.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[F:16][C:4]1[CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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 66827Phenylboronic AcidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 733347338-Fluoro-6-phenyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, grey solid (52 mg, 74%), MS (ISP) m/z=281.3 [(M+H)+], mp 236.5° 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 phenylboronic acid (39.6 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-c3f7339ff66c40bfb71ecd2b1ed22c8b
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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