(Pyridin-4-yl)boronic acid → 8-Fluoro-6-pyridin-4-yl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925651Notes

Reaction equation

HRID 925651 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.[N:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>>[F:16][C:4]1[CH:3]=[C:2]([C:20]2[CH:21]=[CH:22][N:17]=[CH:18][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 2734379(Pyridin-4-yl)boronic acidHCID 900369026-Bromo-8-fluoro-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one2×

Product 1

HCID 733355168-Fluoro-6-pyridin-4-yl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

Procedure

The title compound, white solid (44 mg, 63%), MS (ISP) m/z=282.3 [(M+H)+], mp 323.5° 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 pyridine-4-ylboronic acid (39.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-3ec1c0b44c3a4e4f851554c2ea325977
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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