Cesium carbonate → HCID 68870828, 화합물

HRID 730003

반응식

HRID 730003 반응식
[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[N:23]=[C:22]2[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]2=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:5]1[O:6][C:7]([C:18]2[N:23]=[C:22]3[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]3=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 668690432-tert-Butyl-4-(4-fluorophenyl)oxazoleHCID 86063644HCID 86063644, 화합물

생성물 1

HCID 68870828HCID 68870828, 화합물수율 34%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

Bubble with nitrogen a suspension of 2-tert-butyl-4-(4-fluorophenyl)oxazole (0.145 g, 0.66 mmol), 5-bromo-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-ylamine (0.355 g, 1.32 mmol), cesium carbonate (6.06 g, 18.6 mmol), palladium (II) acetate (0.201 g, 10%) and triphenylphosphine (0.14 g, 0.07 mmol) in DMF (1.5 mL). Heat the reaction at 100° C. overnight, cool to RT and partition between EtOAc and saturated aqueous NaCl. Wash the organic layer with saturated aqueous NaCl. Dry with Na2SO4, filter, concentrate, and purify (silica gel chromatography, eluting with 2% of 2M ammonia/MeOH in CH2Cl2 to give the title compound (0.07 g, 34%).

후처리

  1. customBubble with nitrogen
  2. temperatureHeat
  3. customthe reaction at 100° C. overnight
  4. custompartition between EtOAc and saturated aqueous NaCl
  5. washWash the organic layer with saturated aqueous NaCl
  6. dry with materialDry with Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify (silica gel chromatography
  10. washeluting with 2% of 2M ammonia/MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-ebea77b7d7c54cd391eaca0d172e8e47
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582652B2

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