4-Nitrophenylboronic acid → HCID 73335417, compound

HRID 925847Notes

Reaction equation

HRID 925847 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]([C:16]#[N: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]>>[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[CH:7][C:6]=3[CH:5]=[C:4]([C:16]#[N:17])[CH:3]=2)=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

3

Reactant 2

HCID 27735524-Nitrophenylboronic acidHCID 90035900HCID 90035900, compound2×

Product 1

HCID 73335417HCID 73335417, compound

Procedure

The title compound, yellow solid (16 mg, 19%), MS (ISN) m/z=333.4 [(M+H)+], mp 369.5° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 15) (72.5 mg, 0.25 mmol) and commercially available 4-nitro-phenylboronic acid (54.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-f519f3ad758f43b8980956ebd3ab2ed4
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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