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

HRID 1684909ノート

反応式

HRID 1684909 の反応式
[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

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 86651935HCID 86651935、化合物HCID 178418573HCID 178418573、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8909Butyl ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-19c09e8ee7d342f1826867615c0a3420
出典データセット
uspto-grants-2012_04
特許番号
US08148370B2

反応ノート

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