Tolylboronic acid → HCID 90035825, compound

HRID 925873Notes

Reaction equation

HRID 925873 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.B(O)(O)[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1>>[CH3:16][C:7]1[C:6]2[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=[C:2]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=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 79799Tolylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 90035825HCID 90035825, compound

Procedure

The title compound, light yellow solid (67 mg, 85%), MS (ISP) m/z=316.6 [(M+H)+], mp 277° 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 p-tolylboronic acid (44.2 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-a0730882e5cd47c59fd6171e70bbddfd
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

Loading…