Potassium Carbonate → 4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamine

HRID 1446662

반응식

HRID 1446662 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[CH:9][N:10]=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=2)O1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine

생성물 1

HCID 685394114-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenylamine수율 100%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

To a round bottomed flask add 7-chloro-3-iodo-imidazo[1,2-a]pyridine (3.0 g, 0.011 mol), add 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.6 g, 1.1 equiv.), potassium carbonate (4.5 g, 3 equiv.), dioxane (40 mL), and water (20 mL). Deoxygenate this mixture thoroughly with N2 then add dichlorobis(triphenylphosphine)palladium (II) (0.23 g, 0.03 equiv.) and reflux the reaction overnight under N2. Concentrate the reaction to dryness and slurry in DCM. Filter this slurry thru Celite® and wash with DCM. Concentrate the filtrate then purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM) to give a pale grey solid (2.6 g, 100%). MS (ES), m/z 244 (M+1).

후처리

  1. customDeoxygenate this mixture thoroughly with N2
  2. customthe reaction overnight under N2
  3. concentrationConcentrate
  4. customthe reaction to dryness and slurry in DCM
  5. filtrationFilter this slurry thru Celite®
  6. washwash with DCM
  7. concentrationConcentrate the filtrate
  8. customthen purify by silica plug (EtOAc to 5% MeOH: DCM to 10% MeOH: DCM)

출처 및 근거

ORD 기록
ord-6b0cbc677db84ef98bfb4419ea8b46ae
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666879B2

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