Phenylboronic Acid → 3-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrile

HRID 2218033Notes

Reaction equation

HRID 2218033 reaction equation
Br[C:2]1[C:22]([O:23][CH3:24])=[CH:21][C:5]2[N:6]([CH3:20])[C:7](=[O:19])[CH2:8][N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[C:4]=2[CH:3]=1.C1(B(O)O)C=CC=CC=1.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[C:37]=1B(O)O>>[CH3:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][CH3:43])[C:37]=1[C:2]1[C:22]([O:23][CH3:24])=[CH:21][C:5]2[N:6]([CH3:20])[C:7](=[O:19])[CH2:8][N:9]=[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 2734343(2,6-Dimethoxyphenyl)boronic acidHCID 692877383-(7-bromo-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile

Product 1

HCID 574786463-[7-(2,6-Dimethoxy-phenyl)-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrileYield 44%

Procedure

Prepared from 3-(7-bromo-8-methoxy-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-benzonitrile Intermediate 9 using the same method described for Example 1 and instead of using benzene boronic acid, we used 2,6-dimethoxyphenyl boronic acid. The title compound (83 mg) was obtained as a pale green solid, (yield=44%).

Sources & evidence

ORD record
ord-b384d6612da44c19b9dffae85993d420
Source dataset
uspto-grants-2008_08
Patent number
US07410963B2

Reaction notes

Loading…