Cesium carbonate → HCID 68108563、化合物

HRID 474130

反応式

HRID 474130 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][NH:14][C:9]2=[CH:8][C:7]=1[Cl:15])=[O:5])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[F:22][CH:23]([F:26])[CH2:24]I.[NH4+].[Cl-]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[C:10]2[CH:12]=[CH:13][N:14]([CH2:24][CH:23]([F:26])[F:22])[C:9]2=[CH:8][C:7]=1[Cl:15])=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 38335651,1-Difluoro-2-iodoethaneHCID 60058581Ethyl 6-chloro-1H-pyrrolo[3,2-b]pyridine-5-carboxylate

生成物 1

HCID 68108563HCID 68108563、化合物

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 6-chloro-1H-pyrrolo[3,2-b]pyridine-5-carboxylic acid ethyl ester (210 mg, 0.935 mmol) in DMF (10 ml) was added cesium carbonate (457 mg, 1.402 mmol), after 15 min stirring at room temperature 1,1-difluoro-2-iodoethane (538 mg, 2.8 mmol) was added and stirring was continued over night. Tetrabutylammonium iodide (34.5 mg, 0.093 mmol) was added and stirring was continued for another 48 h. To the reaction mixture was added saturated aq. NH4Cl and the mixture was extracted with MTBE (2×). The combined organic layers were washed with half-saturated aq. NaCl, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 20:80) to provide the title compound as yellow solid.

後処理

  1. additionwas added
  2. waitwas continued over night
  3. stirringstirring
  4. extractionthe mixture was extracted with MTBE (2×)
  5. washThe combined organic layers were washed with half-saturated aq. NaCl
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 20:80)

出典と根拠

ORDレコード
ord-7b1797d9289b4b31b92ec45e3274229f
出典データセット
uspto-grants-2014_01
特許番号
US08637508B2

関連ノート

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