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

HRID 1684920Notes

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[CH:17]=[C:18]([CH:21]=[CH:22][C:23]=4[F:24])[CH:19]=[O:20])=[CH:12][N:11]3[CH:25]=2)=[CH:4][CH:3]=1.[CH3:26][Mg]Br.[Cl-].[NH4+]>C(OCC)C.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[CH:17]=[C:18]([CH:19]([OH:20])[CH3:26])[CH:21]=[CH:22][C:23]=4[F:24])=[CH:12][N:11]3[CH:25]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

470 mg of 3-[2-(4-chlorophenyl)imidazo[1,2-a]pyridin-6-yl]-4-fluorobenzaldehyde are placed in a round-bottomed flask and dissolved in 90 ml of diethyl ether and 45 ml of tetrahydrofuran. The solution is cooled to 0° C. with an ice bath and 4 ml of a 1M solution of methylmagnesium bromide in dibutyl ether are added dropwise thereto. The mixture is stirred in the ice bath for 1 h 30 and 22 ml of a saturated aqueous ammonium chloride solution are added. The organic phase is separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel, elution being carried out with a dichloromethane/methanol mixture. 401 mg of compound are obtained.

Workup

additionare added
customThe organic phase is separated
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure
customThe residue obtained
customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record: ord-b3abb4b0f97c4078abba33ab9a98e83c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148370B2

Reaction notes

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