Potassium Carbonate → 3-(4-(pyridin-3-yl)-1H-pyrazol-1-yl)phenol

HRID 1050642Notes

Reaction equation

HRID 1050642 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>Br.O>[N:16]1[CH:17]=[CH:18][CH:19]=[C:14]([C:12]2[CH:11]=[N:10][N:9]([C:5]3[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=3)[CH:13]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 1180074013-(1-(3-methoxyphenyl)-1H-pyrazol-4-yl)pyridine

Product 1

HCID 1180071923-(4-(pyridin-3-yl)-1H-pyrazol-1-yl)phenolYield 109.6%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of 3-(1-(3-methoxyphenyl)-1H-pyrazol-4-yl)pyridine 4 (1.20 g, 4.77 mmol) in hydrogen bromide acid (15 mL, 48%) refluxed (110-120° C.) for 24 hours under an atmosphere of nitrogen. Then the mixture was cooled down to ambient temperature and neutralized with a solution of K2CO3 in water until there was no gas to generate. Then the precipitate was filtered off and washed with water several times. The collected solid was dried in air to afford the product as a brown solid 1.24 g in 99% yield. 1H NMR (DMSO-d6, 400 MHz): δ 6.59 (dt, J=7.2, 2.0 Hz, 1H), 7.11-7.17 (m, 3H), 7.38 (dd, J=7.6, 1.6 Hz, 1H), 8.07 (dt, J=8.0, 2.0 Hz, 1H), 8.15 (s, 1H), 8.33-8.34 (m, 1H), 8.85 (d, J=1.6 Hz, 1H), 8.90 (s, 1H), 9.78 (bs, 1H).

Workup

  1. filtrationThen the precipitate was filtered off
  2. washwashed with water several times
  3. customThe collected solid was dried in air

Sources & evidence

ORD record
ord-ffbb0f00414c4faa9c9c360cb24e79d9
Source dataset
uspto-grants-2016_07
Patent number
US09385329B2

Reaction notes

Loading…