6-(Dimethylamino)pyridine-3-boronic acid → HCID 73335613, compound

HRID 925775Notes

Reaction equation

HRID 925775 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=[C:7]([CH3:16])[C:6]=2[CH:5]=[C:4]([F:17])[CH:3]=1.[CH3:18][N:19]([CH3:29])[C:20]1[N:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>>[CH3:18][N:19]([CH3:29])[C:20]1[N:25]=[CH:24][C:23]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([F:17])[CH:3]=2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 90036178HCID 90036178, compound2×

Product 1

HCID 73335613HCID 73335613, compound

Procedure

The title compound, grey solid (76 mg, 90%), MS (ISP) m/z=339.5 [(M+H)+], mp 259° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-fluoro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 14) (74.3 mg, 0.25 mmol) and commercially available 6-dimethylamino-pyridin-3-ylboronic acid (53.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-2dbd615bc40f4f7982c822332addfe32
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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