3-Cyanophenylboronic acid → HCID 73335896, compound

HRID 925894Notes

Reaction equation

HRID 925894 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.[C:19]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:20]>>[C:19]([C:21]1[CH:26]=[C:25]([C:2]2[C:10]3[N:9]4[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:8]4=[C:7]([CH3:16])[C:6]=3[CH:5]=[C:4]([C:17]#[N:18])[CH:3]=2)[CH:24]=[CH:23][CH:22]=1)#[N:20]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 90036297HCID 90036297, compound2×

Product 1

HCID 73335896HCID 73335896, compound

Procedure

The title compound, white solid (63 mg, 77%), MS (ISP) m/z=325.6 [(M+H)+], mp 266° 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 3-cyanophenylboronic acid (47.8 mg, 0.325 mmol).

Sources & evidence

ORD record
ord-e6686dee18d64fcab8d256b554688238
Source dataset
uspto-grants-2016_03
Patent number
US09284321B2

Reaction notes

Loading…