4-Nitrophenylboronic acid → HCID 90035781, compound

HRID 925727Notes

Reaction equation

HRID 925727 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.[N+:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)([O-:20])=[O:19]>>[Cl:17][C:4]1[CH:3]=[C:2]([C:24]2[CH:25]=[CH:26][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=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 27735524-Nitrophenylboronic acidHCID 90036013HCID 90036013, compound2×

Product 1

HCID 90035781HCID 90035781, compound

Procedure

The title compound, yellow solid (79 mg, 89%), MS (ISP) m/z=356.5 [(M+H)+], mp 313.5° 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 4-nitro-phenylboronic acid (54.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-860d72b5fe134661b4f0f2d43edc46a6
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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