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

HRID 2217999Notes

Reaction equation

HRID 2217999 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]=[CH:38][C:37]=1B(O)O>>[CH3:24][O:23][C:22]1[C:2]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[O:35][CH3:34])=[CH:3][C:4]2[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[N:9][CH2:8][C:7](=[O:19])[N:6]([CH3:20])[C:5]=2[CH:21]=1

Participants

4

Reactant 3

HCID 66827Phenylboronic AcidHCID 27339582-Methoxyphenylboronic 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 111541373-[8-Methoxy-7-(2-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrileYield 50%

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 o-methoxyphenyl boronic acid. The title compound (80 mg) was obtained as a white solid, in 50% yield.

Sources & evidence

ORD record
ord-f18accd5caf04a85a20397a48d2b72f9
Source dataset
uspto-grants-2008_08
Patent number
US07410963B2

Reaction notes

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