4-Nitrophenylboronic acid → HCID 90035993, compound

HRID 925891Notes

Reaction equation

HRID 925891 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]([C:17]#[N:18])[CH:3]=1.[N+:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O-:21])=[O:20]>>[CH3:16][C:7]1[C:6]2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=[C:2]([C:25]3[CH:26]=[CH:27][C:22]([N+:19]([O-:21])=[O:20])=[CH:23][CH:24]=3)[C:10]=2[N:9]2[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]=12

Participants

3

Reactant 2

HCID 27735524-Nitrophenylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035993HCID 90035993, compound

Procedure

The title compound, yellow solid (41 mg, 47%), MS (ISP) m/z=347.5 [(M+H)+], mp 312° C., was prepared in accordance with the general method of example 1 from 6-bromo-10-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-8-carbonitrile (intermediate 16) (76 mg, 0.25 mmol) and commercially available 4-nitro-phenylboronic acid (54.3 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-2a598a530d7448a4aa305e7e64b49894
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

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