3-Chloro-4-hydroxyphenylboronic Acid → 6-((1H-1,2,4-triazol-1-yl)methyl)-3''-chloro-4''-hydroxybiphenyl-3-carbonitrile

HRID 418420Notes

Reaction equation

HRID 418420 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[OH:8].[N:12]1([CH2:17][C:18]2[CH:23]=[C:22](C3C=CC(O)=CC=3)[C:21]([C:31]#[N:32])=[CH:20][CH:19]=2)[CH:16]=[N:15][CH:14]=[N:13]1>>[N:12]1([CH2:17][C:18]2[C:23]([C:4]3[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=3)=[CH:22][C:21]([C:31]#[N:32])=[CH:20][CH:19]=2)[CH:16]=[N:15][CH:14]=[N:13]1

Participants

3

Reactant 2

HCID 221253733-Chloro-4-hydroxyphenylboronic AcidHCID 235857225-((1H-1,2,4-triazol-1-yl)methyl)-4'-hydroxybiphenyl-2-carbonitrile

Product 1

HCID 451416026-((1H-1,2,4-triazol-1-yl)methyl)-3''-chloro-4''-hydroxybiphenyl-3-carbonitrile

Procedure

The title compound was prepared from 15 and 3-chloro-4-hydroxyphenylboronic acid using similar conditions to those described for the synthesis of 19. Chromatography (EtOAc) eluted 52 as a white crystalline solid (0.089 g, 46%), mp 243-245° C.; 1H NMR δH (270 MHz, DMSO-d6) 5.46 (s, 2H), 7.05 (d, J=8.4 Hz, 1H), 7.15-7.23 (m, 2H), 7.44 (d, J=2.2 Hz, 1H), 7.75 (d, J=1.7 Hz, 1H), 7.80 (dd, J=1.7 Hz, 7.9 Hz, 1H), 7.98 (s, 1H), 8.43 (s, 1H) and 10.51 (br s, 1H); LCMS (APCI−) m/z (rel intensity) 311 (35, [37CIM+H]−), 309 (100, [35CIM+H]−); HRMS (ES+) m/z calcd. for C16H12ClN4O [M+H]+: 311.0694, found 311.0689.

Workup

  1. washChromatography (EtOAc) eluted 52 as a white crystalline solid (0.089 g, 46%), mp 243-245° C.

Sources & evidence

ORD record
ord-cc109d5600244505897dc78e6a3f4a7c
Source dataset
uspto-grants-2012_01
Patent number
US08093279B2

Reaction notes

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