3-Cyanophenol → HCID 22613902, compound

HRID 844612Notes

Reaction equation

C(C1C=C(B(O)O)C=CC=1)#N.BrC1C=C(C=C(C)C=1)C(OC)=O.[C:24]([C:26]1[CH:27]=[C:28]([C:32]2[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([C:39]([O:41][CH3:42])=[O:40])[CH:33]=2)[CH:29]=[CH:30][CH:31]=1)#[N:25].C1C(=O)N(Br)C(=O)C1.[OH:51][C:52]1[CH:53]=[C:54]([CH:57]=[CH:58][CH:59]=1)[C:55]#[N:56]>>[C:24]([C:26]1[CH:27]=[C:28]([C:32]2[CH:37]=[C:36]([CH2:38][O:51][C:52]3[CH:59]=[CH:58][CH:57]=[C:54]([C:55]#[N:56])[CH:53]=3)[CH:35]=[C:34]([C:39]([O:41][CH3:42])=[O:40])[CH:33]=2)[CH:29]=[CH:30][CH:31]=1)#[N:25]

Participants

Reactant 5

HCID 133943-Cyanophenol

HCID 67184N-bromobutanimide

HCID 27343253-Cyanophenylboronic acid

HCID 22613903Methyl 3-bromo-5-methylbenzoate

HCID 22613911HCID 22613911, compound

Product 1

HCID 22613902HCID 22613902, compound

Procedure

Analogously to Example 1, by reaction of 3-cyanophenylboronic acid with methyl 3-bromo-5-methylbenzoate the compound methyl 3′-cyano-5-methylbiphenyl-3-carboxylate is obtained. By bromination with NBS and reaction with 3-hydroxybenzonitrile, methyl 3′-cyano-5-(3-cyanophenoxymethyl)biphenyl-3-carboxylate is obtained. Reaction with hydroxylamine and reduction using H2/Raney Ni affords the compound methyl 3′-carbamimidoyl-5-(3-carbamimidoylphenoxymethyl)biphenyl-3-carboxylate. By hydrolysis of the ester with aqueous NaOH, 3′-carbamimidoyl-5-(3-carbamimidoylphenoxymethyl)biphenyl-3-carboxylic acid

Workup

customis obtained

Sources & evidence

ORD record: ord-1ccbfff1cc9d445e9f849fa762c63cfe
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380430B1

Reaction notes

Loading…