6-(Dimethylamino)pyridine-3-boronic acid → HCID 73335612, compound

HRID 925771Notes

Reaction equation

HRID 925771 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]([Cl: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>>[Cl:17][C:4]1[CH:3]=[C:2]([C:23]2[CH:24]=[N:25][C:20]([N:19]([CH3:29])[CH3:18])=[CH:21][CH:22]=2)[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]=1

Participants

3

Reactant 2

HCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 90036013HCID 90036013, compound2×

Product 1

HCID 73335612HCID 73335612, compound

Procedure

The title compound, off-white solid (77 mg, 87%), MS (ISP) m/z=355.5 [(M+H)+], mp 248° C., was prepared in accordance with the general method of example 1 from 6-bromo-8-chloro-10-methyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (intermediate 12) (78.4 mg, 0.25 mmol) and commercially available 6-dimethylamino-pyridin-3-ylboronic acid (53.9 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-b9942e2eac41499daa7161bc42e4be6c
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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