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

HRID 1684909노트

반응식

HRID 1684909 반응식
[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

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 86651935HCID 86651935, 화합물HCID 178418573HCID 178418573, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8909Butyl ether용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-19c09e8ee7d342f1826867615c0a3420
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148370B2

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