Ammonium Chloride → 1-{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorophenyl}ethanol

HRID 1684909Notes

Reaction equation

HRID 1684909 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([F:24])=[C:18]([CH:21]=[CH:22][CH:23]=4)[CH:19]=[O:20])=[CH:12][N:11]3[CH:25]=2)=[CH:4][CH:3]=1.[CH3:26][Mg]Br.[Cl-].[NH4+]>O1CCCC1.C(OCCCC)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]4[C:17]([F:24])=[C:18]([CH:19]([OH:20])[CH3:26])[CH:21]=[CH:22][CH:23]=4)=[CH:12][N:11]3[CH:25]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 86651935HCID 86651935, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 442318561-{3-[2-(4-Chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorophenyl}ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Conditions

Temperature
0 °C

Procedure

170 mg of 3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-2-fluorobenzaldehyde (compound obtained according to protocol described in Example 1.2) are placed under a stream of argon in a round-bottomed flask and dissolved in 30 ml of tetrahydrofuran. The solution is cooled to 0° C. with an ice bath and 2.60 ml of a solution, standardized beforehand at 0.56M, of methylmagnesium bromide in dibutyl ether are added dropwise. The mixture is left stirring in the ice bath for one hour and then 5 ml of a saturated aqueous ammonium chloride solution are added. The organic phase is separated and dried over sodium sulphate. The solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture. 64 mg of compound are obtained. M.p.=193-195° C. 1H NMR spectrum (d6-DMSO, δ in ppm): 1.4 (d, 3H); 5.1 (m, 1H); 5.35 (d, 1H); 7.35 (m, 1H); from 7.45 to 7.65 (m, 5H); 7.7 (d, 1H); 8.05 (d, 2H); 8.5 (s, 1H); 8.75 (s, 1H). M+H=367.

Workup

  1. additionare added dropwise
  2. waitThe mixture is left
  3. customThe organic phase is separated
  4. dry with materialdried over sodium sulphate
  5. customThe solvent is evaporated under reduced pressure
  6. customThe residue is purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-19c09e8ee7d342f1826867615c0a3420
Source dataset
uspto-grants-2012_04
Patent number
US08148370B2

Reaction notes

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