Cesium carbonate → HCID 68870828、化合物

HRID 730003

反応式

HRID 730003 の反応式
[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]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 668690432-tert-Butyl-4-(4-fluorophenyl)oxazoleHCID 86063644HCID 86063644、化合物

生成物 1

HCID 68870828HCID 68870828、化合物収率 34%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ebea77b7d7c54cd391eaca0d172e8e47
出典データセット
uspto-grants-2009_09
特許番号
US07582652B2

関連ノート

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