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

HRID 985520ノート

反応式

HRID 985520 の反応式
[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

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f37837de394d4e878c1b588da6122c80
出典データセット
uspto-grants-2005_03
特許番号
US06872731B2

反応ノート

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