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

HRID 2218000Notes

Reaction equation

HRID 2218000 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][C:39](B(O)O)=[CH:38][CH:37]=1>>[CH3:24][O:23][C:22]1[C:2]([C:39]2[CH:40]=[CH:41][C:36]([O:35][CH3:34])=[CH:37][CH:38]=2)=[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 201262(4-Methoxyphenyl)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 112469003-[8-Methoxy-7-(4-methoxy-phenyl)-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl]-benzonitrileYield 53%

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 p-methoxyphenyl boronic acid. The title compound (85 mg) was obtained as a white solid, (yield=53%).

Sources & evidence

ORD record
ord-e2d117dd9a6549ea93dc2f32bd3dac17
Source dataset
uspto-grants-2008_08
Patent number
US07410963B2

Reaction notes

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