Cesium carbonate → HCID 68108563, 화합물

HRID 474130

반응식

HRID 474130 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 68108563HCID 68108563, 화합물

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7b1797d9289b4b31b92ec45e3274229f
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637508B2

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