Tolylboronic acid → HCID 90036847, compound

HRID 925707Notes

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.B(O)(O)[C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=1>>[Cl:17][C:4]1[CH:3]=[C:2]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=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

Reactant 2

HCID 79799Tolylboronic acid

HCID 90036013HCID 90036013, compound2×

Product 1

HCID 90036847HCID 90036847, compound

Procedure

The title compound, light brown solid (72 mg, 89%), MS (ISP) m/z=325.5 [(M+H)+], mp 251.5° 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 p-tolylboronic acid (44.2 mg, 0.325 mmol).

Sources & evidence

ORD record: ord-72b92505eadb4e318a0466a410fe71a5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09284321B2

Reaction notes

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