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Sodium Carbonate → 3,6-Bis-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383287
노트
인쇄 미리보기

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HRID 383287 반응식
Br[C:2]1[N:6]2[CH:7]=[C:8](Br)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.CO[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][C:19]=1B(O)O.[C:23]([O-:26])([O-])=O.[Na+].[Na+].O1[CH2:34][CH2:33][O:32][CH2:31]C1>O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:34]=[C:9]([C:2]2[N:6]3[CH:7]=[C:8]([C:19]4[CH:14]=[CH:15][N:16]=[C:17]([O:26][CH3:23])[CH:18]=4)[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:10]=[CH:5][N:4]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 467390193-Methoxypyridine-4-boronic acidHCID 467390843,6-Dibromoimidazo[1,2-a]pyridine2회

생성물 1

HCID 252619073,6-Bis-(2-methoxy-pyridin-4-yl)-imidazo[1,2-a]pyridine

시약·촉매·용매 2

HCID 178419050
HCID 178419050, 화합물
촉매
HCID 962Water용매2회

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온도
100 °C

실험 절차

To a solution of 3-bromo-6-bromo-imidazo[1,2-a]pyridine (Intermediate H) (1 eq, 0.72 mmol, 0.2 g), 3-methoxypyrid-4-yl boronic acid (1.0 eq, 0.72 mmol, 0.11 g), Na2CO3 (2 eq, 1.44 mmol, 152 mg) in dioxane (45 ml) and water (13.5 ml) under inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 0.07 mmol, 50 mg). The reaction mixture is heated at 100° C. for 2 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 25-75% ethyl acetate in iso-hexane to afford the title compound; [M+H]+=333

후처리

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography on silica eluting with 25-75% ethyl acetate in iso-hexane

출처 및 근거

ORD 기록
ord-af509ed55152452baa4d792b69e5fe9a
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367662B2

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