Hydrogen Bromide → HCID 178515960, compound

HRID 403519Notes

Reaction equation

HRID 403519 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[N:11]=2)=[CH:8][C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:6]1.Br.C(=O)(O)[O-].[Na+]>>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[CH2:4][N:5]1[C:9]([C:10]2[N:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)=[N:6]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 66633736HCID 66633736, compound

Product 1

HCID 178515960HCID 178515960, compoundYield 70%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-pyrazol-5-yl)-6-methoxypyridine (Compound I-25; 85.6 mg) and hydrobromic acid (1.2 ml, 33 wt % in acetic acid) in a sealed flask was heated to 100° C. for 18 h. The mixture was poured into ice and basified with saturated solution of sodium bicarbonate. The mixture was extracted with ethyl acetate. The organic portions were combined, dried (with Na2SO4), filtered, and concentrated under vacuum to give crude oil. The crude oil was purified using SiO2 chromatography using ethyl acetate/methanol as gradient to give 6-(1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-pyrazol-5-yl)pyridin-2-ol (Compound I-79, 70%) as off white solid. 1H NMR (400 MHz, CDCl3) δ 11.54 (bs, 1H), 8.67-8.62 (m, 1H), 8.00-7.94 (m, 1H), 7.74 (td, 1H), 7.42-7.36 (m, 1H), 7.28-7.15 (m, 3H), 7.05-6.93 (m, 3H), 6.56 (d, 1H), 6.27 (d, 1H), 5.61 (s, 2H) ppm.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialdried (with Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give crude oil
  6. customThe crude oil was purified

Sources & evidence

ORD record
ord-43e303c632e84a9e8c3a9f2140071955
Source dataset
uspto-grants-2014_06
Patent number
US08748442B2

Reaction notes

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