Cesium carbonate → Ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1844192노트

반응식

HRID 1844192 반응식
[OH:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[CH2:19][C:20]1[C:25]([F:26])=[CH:24][N:23]=[CH:22][C:21]=1[F:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:27][C:21]1[CH:22]=[N:23][CH:24]=[C:25]([F:26])[C:20]=1[CH2:19][O:1][C:2]1[C:3]2[N:4]([C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([CH3:12])[N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 86717883Ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylateHCID 867182084-(Chloromethyl)-3,5-difluoropyridine

생성물 1

HCID 86718219Ethyl 8-[(3,5-difluoropyridine-4-yl)methoxy]-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

5.0 g (21.34 mmol) of ethyl 8-hydroxy-2,6-dimethylimidazo[1,2-a]pyridine-3-carboxylate from Example 87A and 3.83 g (23.48 mmol) of 4-(chloromethyl)-3,5-difluoropyridine from Example 115A were initially charged in 306 ml of abs. DMF, and 20.8 g (64.03 mmol) of caesium carbonate were added. The reaction mixture was stirred at 60° C. overnight. The reaction mixture, cooled to RT, was filtered, washed with ethyl acetate and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient=4:1 to 2:1). This gave 5.40 g (70% of theory) of the target compound.

후처리

  1. temperatureThe reaction mixture, cooled to RT
  2. filtrationwas filtered
  3. washwashed with ethyl acetate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate gradient=4:1 to 2:1)

출처 및 근거

ORD 기록
ord-10789e9e581a42f49dda858e6a82620f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946215B2

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