Phenylboronic Acid → 2-Chloro-4-(4-phenoxyphenyl)nicotinonitrile

HRID 81018Notes

Reaction equation

[Cl:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:3]=1[C:4]#[N:5].[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[C:3]=1[C:4]#[N:5]

Participants

Reactant 2

HCID 66827Phenylboronic Acid

HCID 135741338HCID 135741338, compound

Product 1

HCID 866656782-Chloro-4-(4-phenoxyphenyl)nicotinonitrileYield 90%

Procedure

Following conditions described in Step 1 of Example 3, 2-chloro-4-(4-hydroxyphenyl)nicotinonitrile was reacted with phenylboronic acid to give 2-chloro-4-(4-phenoxyphenyl)nicotinonitrile (60 mg, 90% yield). 1H NMR (500 MHz, CDCl3) 8 ppm 8.56 (1H, δ, J=5.22 Hz), 7.53-7.67 (2H, m), 7.37-7.49 (3H, m), 7.22 (1H, t, J=7.42 Hz), 7.09-7.16 (4H, m); MS (ES+) m/z: 307 (M+H); LC retention time: 3.863 min (analytical HPLC Method A).

Sources & evidence

ORD record: ord-3621bb685b0e4d03bab60adf91c4dbd0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846673B2

Reaction notes

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