Isopropanol → HCID 44133936, compound

HRID 1028190Notes

Reaction equation

HRID 1028190 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([C:9]2[N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:12]=[N:11][CH:10]=2)O)=[CH:3][CH:2]=1.[CH3:33][CH:34](O)[CH3:35].[OH-].[Na+]>I.C(Cl)(Cl)Cl>[NH:13]1[C:9]([CH:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[CH2:33][C:34]2[CH:35]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:10][N:11]=[CH:12]1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 57437676HCID 57437676, compound

Product 1

HCID 44133936HCID 44133936, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 24841Hydrogen iodideSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of pyridin-4-yl(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 4) (526 g, 1.03 mmol) in 57% aqueous HI (10 mL) and iPrOH (2 mL) was added red phosphorus (318 mg, 10.3 mmol) in a resealable tube was heated at 160° C. for 16 h. The mixture was then cooled to room temperature and poured into ice-water, which was then basified with NaOH and diluted with CHCl3. The residue was isolated in a typical aqueous workup using CHCl3 and purified by MPLC with 5 to 15% MeOH: CH2Cl2 to give 4-(1-(1H-imidazol-5-yl)-2-phenylethyl)pyridine (AGN214418) as a solid, 36 mg. 1HNMR (CD3OD, 300 MHz) δ 6.98 (s, 1H), 7.20-7.11, (m, 9H), 7.61 (s, 1H), 4.38 (t, J=9 Hz, 1H), 3.43 (dd, J=6 Hz, 12 Hz, 1H), 3.19 (dd, J=9 Hz, 15 Hz, 1H).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by MPLC with 5 to 15% MeOH

Sources & evidence

ORD record
ord-b5fb95ec777047f284c28ca33757d6ef
Source dataset
uspto-grants-2014_05
Patent number
US08735438B2

Reaction notes

Loading…