4-(Hydroxymethyl)benzeneboronic acid → HCID 58345064, compound

HRID 1887994Notes

Reaction equation

HRID 1887994 reaction equation
[NH2:1][C:2]1[C:7]([C:8]2[N:17]([C:18]3[CH:33]=[CH:32][C:21]([CH2:22][NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[C:11]3=[N:12][CH:13]=[C:14](Br)[CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:1][C:2]1[C:7]([C:8]2[N:17]([C:18]3[CH:33]=[CH:32][C:21]([CH2:22][NH:23][C:24](=[O:31])[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[C:11]3=[N:12][CH:13]=[C:14]([C:39]4[CH:40]=[CH:41][C:36]([CH2:35][OH:34])=[CH:37][CH:38]=4)[CH:15]=[C:10]3[N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 58345070HCID 58345070, compound

Product 1

HCID 58345064HCID 58345064, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

N-(4-(2-(2-aminopyridin-3-yl)-6-bromo-3H-imidazo[4,5-b]pyridin-3-yl)benzyl)benzamide (62.4 mg, 0.125 mmol), CsCO3 (40.6 mg, 0.125 mmol), Pd(PPh3)4 (14.4 mg, 0.013 mmol) and 4-(hydroxymethyl)phenylboronic acid (33.5 mg, 0.25 mmol) were dissolved in DMF (3 mL). The reaction mixture was heated to 150° C. for 15 min and after cooling to room temperature filtered through a Bakerbond filtration column. The reaction mixture was directly purified by reversed phase HPLC to give the desired product as the mono-TFA salt (21 mg, 25% yield). Mp. 171-174° C.; 400 M Hz 1H NMR (DMSO-d6) δ: 9.15 (t, J=6 Hz, 1H), 8.68-8.64 (m, 1H), 8.5-8.47 (m, 1H), 8.08-8.03 (m, 1H), 7.96-7.9 (m, 3H), 7.77-7.72 (m, 3H), 7.6-7.42 (m, 8H), 4.63-4.53 (m, 4H); LCMS [M+H]: 527.

Workup

  1. temperatureafter cooling to room temperature
  2. filtrationfiltered through a Bakerbond filtration column
  3. customThe reaction mixture was directly purified by reversed phase HPLC

Sources & evidence

ORD record
ord-d402ae58676d4b94a8a2abafb44a36f6
Source dataset
uspto-grants-2013_08
Patent number
US08501770B2

Reaction notes

Loading…