Methanol → 1-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanol

HRID 985520노트

반응식

HRID 985520 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]=[O:23])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1.[CH3:24][Mg]Br.CO>O1CCCC1>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:13]3[N:17]4[CH:18]=[CH:19][C:20]([CH:22]([OH:23])[CH3:24])=[CH:21][C:16]4=[N:15][CH:14]=3)[CH:10]=[CH:11][CH:12]=2)[CH:2]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 99441283-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-alpha]pyridine-7-carboxaldehydeHCID 178418573HCID 178418573, 화합물

생성물 2

HCID 222AmmoniaHCID 99228911-[3-(3-(Pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyridin-7-yl]ethanol수율 57%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-[3-(Pyridin-3-yl)phenyl]imidazo[1,2-α]pyridine-7-carboxaldehyde (100 mg, 0.33 mmol) in tetrahydrofuran (10 ml) was cooled to −78° C. before adding methylmagnesium bromide (1.3 ml of 0.3M solution in diethyl ether) dropwise over 10 min. Once addition was complete the reaction was allowed to warm to ambient temperature and stirring continued for 16 h. Methanol (1 ml) was added and the mixture partitioned between ethyl acetate and 10% ammonium chloride solution. The organic layer was washed with brine, dried over sodium sulphate and concentrated to give a yellow oil. This oil was purified by preparative thin layer chromatography eluting with dichloromethane/methanol/conc. ammonia (95:5:0.5) to afford the title compound (59 mg, 57%) as a white foam. 1H NMR (360 MHz, CDCl3) δH 1.55 (3H, d, J 6), 4.97 (1H, q, J 6), 6.91 (1H, dd, J 2 and 7) 7.37-7.43 (1H, m), 7.56-7.67 (4H, m), 7.65-7.74 (2H, m), 7.89-7.94 (1H, m), 8.33 (1H, d, J 7), 8.60-8.65 (1H, m), 8.89 (1H, s); m/z (ES+) 316 (M++H).

후처리

  1. additionOnce addition
  2. customthe mixture partitioned between ethyl acetate and 10% ammonium chloride solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customThis oil was purified by preparative thin layer chromatography
  8. washeluting with dichloromethane/methanol/conc

출처 및 근거

ORD 기록
ord-f37837de394d4e878c1b588da6122c80
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06872731B2

반응 노트

불러오는 중…