Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylate → Ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate

HRID 2229205노트

반응식

HRID 2229205 반응식
[CH:1]([C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Mg]Br>C1COCC1.C([O-])(O)=O.[Na+]>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[CH:1]([OH:2])[C:3]1[N:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]2=[N:5][C:4]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 2

HCID 10704014Ethyl 3-formylimidazo[1,2-a]pyridine-2-carboxylateHCID 178492591HCID 178492591, 화합물

생성물 1

HCID 18466904Ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate수율 57%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of 872 mg (4.0 mmol) of ethyl 3-formyl-imidazolo[1,2-a]pyridine-2-carboxylate in 40 mL THF is treated at −50° C. with 4 mL (4.0 mmol) 1M 2,5-dimethoxyphenylmagnesium bromide in THF. The temperature is allowed to reach −10° C. over 3 hr, diluted with 25 mL sat. NaHCO3 and extracted with 3×50 mL ethyl acetate. The combined organics are washed with 50 mL water and 50 mL brine. The resulting organic layer is dried over anhydrous MgSO4 and the solvent removed in vacuo. The residue is flash chromatographed with 1% methanol in dichloromethane to afford 800 mg (57%) ethyl 3-[(2,5-dimethoxyphenyl)hydroxymethyl]-imidazolo[1,2-a]pyridine-2-carboxylate.

후처리

  1. extractionextracted with 3×50 mL ethyl acetate
  2. washThe combined organics are washed with 50 mL water and 50 mL brine
  3. dry with materialThe resulting organic layer is dried over anhydrous MgSO4
  4. customthe solvent removed in vacuo
  5. customchromatographed with 1% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-e572c8631e11486786ca70a1b58f44aa
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06420365B1

반응 노트

불러오는 중…